Organic electroluminescent materials and devices

ABSTRACT

A compound having a formula M(L A ) x (L B ) y (L C ) where ligand L A  is 
     
       
         
         
             
             
         
       
     
     ligand L B  is 
     
       
         
         
             
             
         
       
     
     and ligand L C  is 
     
       
         
         
             
             
         
       
     
     is disclosed. In the formula, M is a heavy metal, x and y are 1, or 2, and z is 0, 1, or 2, where x+y+z is the oxidation state of metal M. R 1 , R 2 , R 3 , and R 4  are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl, and at least one of R 1 , R 2 , R 3 , and R 4  has at least two C atoms. Rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; at least one R B  has the following structure 
     
       
         
         
             
             
         
       
     
     and at least one of R 6 , R 7 , and R 8  is alkyl, cycloalkyl, halide, and combinations thereof. Any adjacent substitutents of R A , R B , R C , and R D  are optionally joined to form a ring.

PARTIES TO A JOINT RESEARCH AGREEMENT

The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.

FIELD OF THE INVENTION

The present invention relates to compounds for use as emitters and devices, such as organic light emitting diodes, including the same.

BACKGROUND

Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.

OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.

One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)₃, which has the following structure:

In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.

As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.

As used herein, “solution processable” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.

A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.

As used herein, and as would be generally understood by one skilled in the art, a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.

As used herein, and as would be generally understood by one skilled in the art, a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.

More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.

SUMMARY OF THE INVENTION

According to an embodiment, a compound is provided that has a structure according to formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z):

wherein the ligand L_(A) is

wherein the ligand L_(B) is

and

wherein the ligand L_(C) is

In the compounds of formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z):

M is a metal having an atomic number greater than 40;

x is 1, or 2;

y is 1, or 2;

z is 0, 1, or 2;

x+y+z is the oxidation state of the metal M;

R¹, R², R³, and R⁴ are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

-   -   at least one of R¹, R², R³, and R⁴ has at least two C atoms;

R⁵ is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

R_(A), R_(C), and R_(D) each independently represent mono, di, tri, or tetra substitution, or no substitution;

R_(B) represents mono, di, tri, tetra, penta, or hexa substitution;

at least one R_(B) has the following structure:

each of R_(A), R_(B), R_(C), and R_(D) are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any adjacent substitutents of R_(A), R_(B), R_(C), and R_(D) are optionally joined to form a ring;

R⁶, R⁷, and R⁸ are independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof; and

at least one of R⁶, R⁷, and R⁸ is not hydrogen or deuterium.

According to another embodiment, a first device comprising a first organic light emitting device is also provided. The first organic light emitting device can include an anode, a cathode, and an organic layer, disposed between the anode and the cathode. The organic layer can include a compound of formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z). The first device can be a consumer product, an organic light-emitting device, and/or a lighting panel.

Formulations containing a compound of formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z) are also provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an organic light emitting device.

FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.

FIG. 3 shows the structure of the ligands of formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z) as disclosed herein.

DETAILED DESCRIPTION

Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.

More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), which are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.

FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.

More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F₄-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.

The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.

Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.

Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise a single layer, or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, a large area wall, theater or stadium screen, or a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.

The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.

The term “halo” or “halogen” as used herein includes fluorine, chlorine, bromine, and iodine.

The term “alkyl” as used herein contemplates both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. Additionally, the alkyl group may be optionally substituted.

The term “cycloalkyl” as used herein contemplates cyclic alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, and the like. Additionally, the cycloalkyl group may be optionally substituted.

The term “alkenyl” as used herein contemplates both straight and branched chain alkene radicals. Preferred alkenyl groups are those containing two to fifteen carbon atoms. Additionally, the alkenyl group may be optionally substituted.

The term “alkynyl” as used herein contemplates both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.

The terms “aralkyl” or “arylalkyl” as used herein are used interchangeably and contemplate an alkyl group that has as a substituent an aromatic group. Additionally, the aralkyl group may be optionally substituted.

The term “heterocyclic group” as used herein contemplates aromatic and non-aromatic cyclic radicals. Hetero-aromatic cyclic radicals also means heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 or 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperdino, pyrrolidino, and the like, and cyclic ethers, such as tetrahydrofuran, tetrahydropyran, and the like. Additionally, the heterocyclic group may be optionally substituted.

The term “aryl” or “aromatic group” as used herein contemplates single-ring groups and polycyclic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Additionally, the aryl group may be optionally substituted.

The term “heteroaryl” as used herein contemplates single-ring hetero-aromatic groups that may include from one to three heteroatoms, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine and pyrimidine, and the like. The term heteroaryl also includes polycyclic hetero-aromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Additionally, the heteroaryl group may be optionally substituted.

The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl may be optionally substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

As used herein, “substituted” indicates that a substituent other than H is bonded to the relevant position, such as carbon. Thus, for example, where R¹ is mono-substituted, then one R¹ must be other than H. Similarly, where R¹ is di-substituted, then two of R¹ must be other than H. Similarly, where R¹ is unsubstituted, R¹ is hydrogen for all available positions.

The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.

It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.

According to one embodiment, a compound having a structure according to formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z):

wherein the ligand L_(A) is

wherein the ligand L_(B) is

and

wherein the ligand L_(C) is

is disclosed. In the compound of formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z):

M is a metal having an atomic number greater than 40;

x is 1, or 2;

y is 1, or 2;

z is 0, 1, or 2;

x+y+z is the oxidation state of the metal M;

R¹, R², R³, and R⁴ are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

-   -   at least one of R¹, R², R³, and R⁴ has at least two C atoms;

R⁵ is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

R_(A), R_(C), and R_(D) each independently represent mono, di, tri, or tetra substitution, or no substitution;

R_(B) represents mono, di, tri, tetra, penta, or hexa substitution;

at least one R_(B) has the following structure:

each of R_(A), R_(B), R_(C), and R_(D) are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any adjacent substitutents of R_(A), R_(B), R_(C), and R_(D) are optionally joined to form a ring;

R⁶, R⁷, and R⁸ are independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof; and

at least one of R⁶, R⁷, and R⁸ is not hydrogen or deuterium.

In some embodiments, both R⁶ & R⁸ are alkyl. In some embodiments, R⁶ & R⁸ are the same and are both alkyl. In some embodiments, at least one of R⁶, R⁷, and R⁸ comprises at least 2 C atoms. In some embodiments, at least one of R⁶, R⁷, and R⁸ comprises at least 3 C atoms, while at least one of R⁶, R⁷, and R⁸ comprises at least 4 C atoms in other embodiments.

In some embodiments, R_(B) is mono substituted. In some embodiments, R_(B) is at least disubstituted.

In some embodiments, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In some embodiments, M is Ir.

In some embodiments, ring A is benzene. In some embodiments, ring C is benzene and ring D is pyridine.

In some embodiments, R⁵ is selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof. In some embodiments, R⁵ is hydrogen.

In some embodiments, R¹, R², R³, and R⁴ are alkyl or cycloalkyl. In some such embodiments, R¹, R², R³, and R⁴ are independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof. In some embodiments, R⁶, R⁷, and R⁸ are independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, partially or fully fluorinated variants thereof, fluorine, and combinations thereof.

In some embodiments, the compound has the structure of formula 1:

In some embodiments of formula 1, n is 1 or 2. In some embodiments of formula 1, n is 2.

In some embodiments, R_(A) is selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof.

In some embodiments, the compound has the structure of formula 2:

In some embodiments of formula 2. R⁹, and R¹⁰ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof.

In some embodiments, ligand L_(A) is selected from the group consisting of L_(A1) to L_(A104) listed below:

L_(A1) through L_(A13), each represented by the formula

wherein in L_(A1): R⁷═CH₃, and R⁶═R⁸═H, in L_(A2): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A3): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A4): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A5): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A6): R⁷═F, and R⁶═R⁸═H, in L_(A7): R⁷═H, and R⁶═R₈═CH₃,

in L_(A8): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A9): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A10): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A11): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A12): R⁷═H, and R⁶═R⁸═F, and in L_(A13): R⁶═R⁷═R⁸═CH₃,

L_(A14) through L_(A26), each represented by the formula

wherein in L_(A14): R⁷═CH₃, and R⁶═R⁸═H, in L_(A14): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A16): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A17): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A18): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A19): R⁷═F, and R⁶═R⁸═H, in L_(A20): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A21): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A22): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A23): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A24): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A25): R⁷═H, and R⁶═R⁸═F, and in L_(A26): R⁶═R⁷═R⁸═CH₃,

L_(A27) through L_(A39), each represented by the formula

wherein in L_(A27): R⁷═CH₃, and R⁶═R⁸═H, in L_(A28): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A29): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A30): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A31): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A32): R⁷═F, and R⁶═R⁸═H, in L_(A33): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A34): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A35): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A36): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A37): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A38): R⁷═H, and R⁶═R⁸═F, and in L_(A39): R⁶═R⁷═R⁸═CH₃,

L_(A40) through L_(A52), each represented by the formula

wherein in L_(A40): R⁷═CH₃, and R⁶═R⁸═H, in L_(A41): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A42): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A43): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A44): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A45): R⁷═F, and R⁶═R⁸═H, in L_(A46): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A47): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A48): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A49): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A50): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A51): R⁷═H, and R⁶═R⁸═F, and in L_(A52): R⁶═R⁷═R⁸═CH₃,

L_(A53) through L_(A65), each represented by the formula

wherein in L_(A53): R⁷═CH₃, and R⁶═R⁸═H, in L_(A54): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A55): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A56): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A57): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A58): R⁷═F, and R⁶═R⁸═H, in L_(A59): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A60): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A61): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A62): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A63): R⁷═H, and R⁶═R⁸=neopenty,

in L_(A64): R⁷═H, and R⁶═R⁸═F, and in L_(A65): R⁶═R⁷═R⁸═CH₃,

L_(A66) through L_(A78), each represented by the formula

wherein in L_(A66): R⁷═CH₃, and R⁶═R⁸═H, in L_(A67): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A68): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A69): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A70): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A71): R⁷═F, and R⁶═R⁸═H, in L_(A72): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A73): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A74): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A75): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A76): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A77): R⁷═H, and R⁶═R⁸═F, and in L_(A78): R⁶═R⁷═R⁸═CH₃,

L_(A79) through L_(A91), each represented by the formula

wherein in L_(A79): R⁷═CH₃, and R⁶═R⁸═H, in L_(A80): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A81): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A82): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A83): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A84): R⁷═F, and R⁶═R⁸═H, in L_(A85): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A86): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A87): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A88): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A89): R⁷═H, and R⁶═R⁸ neopentyl,

in L_(A90): R⁷═H, and R⁶═R⁸═F, and in L_(A91): R⁶═R⁷═R⁸═CH₃, and

L_(A92) through L_(A104), each represented by the formula

wherein in L_(A92): R⁷═CH₃, and R⁶═R⁸═H, in L_(A93): R⁷=isopropyl, and R⁶═R⁸═H, in L_(A94): R⁷=isobutyl, and R⁶═R⁸═H, in L_(A95): R⁷=cyclopentyl, and R⁶═R⁸═H, in L_(A96): R⁷=neopentyl, and R⁶═R⁸═H,

in L_(A97): R⁷═F, and R⁶═R⁸═H, in L_(A98): R⁷═H, and R⁶═R⁸═CH₃,

in L_(A99): R⁷═H, and R⁶═R⁸=isopropyl, in L_(A100): R⁷═H, and R⁶═R⁸=isobutyl, in L_(A101): R⁷═H, and R⁶═R⁸=cyclopentyl, in L_(A102): R⁷═H, and R⁶═R⁸=neopentyl,

in L_(A103): R⁷═H, and R⁶═R⁸═F, and in L_(A104): R⁶═R⁷═R⁸═CH₃,

In some embodiments, ligand L_(B) is selected from the group consisting of L_(B1)-L_(B9) listed below:

In some embodiments, the compound comprises ligand L_(A) and ligand L_(B) selected from the group consisting of:

Compound Number L_(A) L_(B) 1 L_(A1) L_(B1) 2 L_(A2) L_(B1) 3 L_(A3) L_(B1) 4 L_(A4) L_(B1) 5 L_(A5) L_(B1) 6 L_(A6) L_(B1) 7 L_(A7) L_(B1) 8 L_(A8) L_(B1) 9 L_(A9) L_(B1) 10 L_(A10) L_(B1) 11 L_(A11) L_(B1) 12 L_(A12) L_(B1) 13 L_(A13) L_(B1) 14 L_(A14) L_(B1) 15 L_(A15) L_(B1) 16 L_(A16) L_(B1) 17 L_(A17) L_(B1) 18 L_(A18) L_(B1) 19 L_(A19) L_(B1) 20 L_(A20) L_(B1) 21 L_(A21) L_(B1) 22 L_(A22) L_(B1) 23 L_(A23) L_(B1) 24 L_(A24) L_(B1) 25 L_(A25) L_(B1) 26 L_(A26) L_(B1) 27 L_(A27) L_(B1) 28 L_(A28) L_(B1) 29 L_(A29) L_(B1) 30 L_(A30) L_(B1) 31 L_(A31) L_(B1) 32 L_(A32) L_(B1) 33 L_(A33) L_(B1) 34 L_(A34) L_(B1) 35 L_(A35) L_(B1) 36 L_(A36) L_(B1) 37 L_(A37) L_(B1) 38 L_(A38) L_(B1) 39 L_(A39) L_(B1) 40 L_(A40) L_(B1) 41 L_(A41) L_(B1) 42 L_(A42) L_(B1) 43 L_(A43) L_(B1) 44 L_(A44) L_(B1) 45 L_(A45) L_(B1) 46 L_(A46) L_(B1) 47 L_(A47) L_(B1) 48 L_(A48) L_(B1) 49 L_(A49) L_(B1) 50 L_(A50) L_(B1) 51 L_(A51) L_(B1) 52 L_(A52) L_(B1) 53 L_(A53) L_(B1) 54 L_(A54) L_(B1) 55 L_(A55) L_(B1) 56 L_(A56) L_(B1) 57 L_(A57) L_(B1) 58 L_(A58) L_(B1) 59 L_(A59) L_(B1) 60 L_(A60) L_(B1) 61 L_(A61) L_(B1) 62 L_(A62) L_(B1) 63 L_(A63) L_(B1) 64 L_(A64) L_(B1) 65 L_(A65) L_(B1) 66 L_(A66) L_(B1) 67 L_(A67) L_(B1) 68 L_(A68) L_(B1) 69 L_(A69) L_(B1) 70 L_(A70) L_(B1) 71 L_(A71) L_(B1) 72 L_(A72) L_(B1) 73 L_(A73) L_(B1) 74 L_(A74) L_(B1) 75 L_(A75) L_(B1) 76 L_(A76) L_(B1) 77 L_(A77) L_(B1) 78 L_(A78) L_(B1) 79 L_(A79) L_(B1) 80 L_(A80) L_(B1) 81 L_(A81) L_(B1) 82 L_(A82) L_(B1) 83 L_(A83) L_(B1) 84 L_(A84) L_(B1) 85 L_(A85) L_(B1) 86 L_(A86) L_(B1) 87 L_(A87) L_(B1) 88 L_(A88) L_(B1) 89 L_(A89) L_(B1) 90 L_(A90) L_(B1) 91 L_(A91) L_(B1) 92 L_(A92) L_(B1) 93 L_(A93) L_(B1) 94 L_(A94) L_(B1) 95 L_(A95) L_(B1) 96 L_(A96) L_(B1) 97 L_(A97) L_(B1) 98 L_(A98) L_(B1) 99 L_(A99) L_(B1) 100 L_(A100) L_(B1) 101 L_(A101) L_(B1) 102 L_(A102) L_(B1) 103 L_(A103) L_(B1) 104 L_(A104) L_(B1) 105 L_(A1) L_(B2) 106 L_(A2) L_(B2) 107 L_(A3) L_(B2) 108 L_(A4) L_(B2) 109 L_(A5) L_(B2) 110 L_(A6) L_(B2) 111 L_(A7) L_(B2) 112 L_(A8) L_(B2) 113 L_(A9) L_(B2) 114 L_(A10) L_(B2) 115 L_(A11) L_(B2) 116 L_(A12) L_(B2) 117 L_(A13) L_(B2) 118 L_(A14) L_(B2) 119 L_(A15) L_(B2) 120 L_(A16) L_(B2) 121 L_(A17) L_(B2) 122 L_(A18) L_(B2) 123 L_(A19) L_(B2) 124 L_(A20) L_(B2) 125 L_(A21) L_(B2) 126 L_(A22) L_(B2) 127 L_(A23) L_(B2) 128 L_(A24) L_(B2) 129 L_(A25) L_(B2) 130 L_(A26) L_(B2) 131 L_(A27) L_(B2) 132 L_(A28) L_(B2) 133 L_(A29) L_(B2) 134 L_(A30) L_(B2) 135 L_(A31) L_(B2) 136 L_(A32) L_(B2) 137 L_(A33) L_(B2) 138 L_(A34) L_(B2) 139 L_(A35) L_(B2) 140 L_(A36) L_(B2) 141 L_(A37) L_(B2) 142 L_(A38) L_(B2) 143 L_(A39) L_(B2) 144 L_(A40) L_(B2) 145 L_(A41) L_(B2) 146 L_(A42) L_(B2) 147 L_(A43) L_(B2) 148 L_(A44) L_(B2) 149 L_(A45) L_(B2) 150 L_(A46) L_(B2) 151 L_(A47) L_(B2) 152 L_(A48) L_(B2) 153 L_(A49) L_(B2) 154 L_(A50) L_(B2) 155 L_(A51) L_(B2) 156 L_(A52) L_(B2) 157 L_(A53) L_(B2) 158 L_(A54) L_(B2) 159 L_(A55) L_(B2) 160 L_(A56) L_(B2) 161 L_(A57) L_(B2) 162 L_(A58) L_(B2) 163 L_(A59) L_(B2) 164 L_(A60) L_(B2) 165 L_(A61) L_(B2) 166 L_(A62) L_(B2) 167 L_(A63) L_(B2) 168 L_(A64) L_(B2) 169 L_(A65) L_(B2) 170 L_(A66) L_(B2) 171 L_(A67) L_(B2) 172 L_(A68) L_(B2) 173 L_(A69) L_(B2) 174 L_(A70) L_(B2) 175 L_(A71) L_(B2) 176 L_(A72) L_(B2) 177 L_(A73) L_(B2) 178 L_(A74) L_(B2) 179 L_(A75) L_(B2) 180 L_(A76) L_(B2) 181 L_(A77) L_(B2) 182 L_(A78) L_(B2) 183 L_(A79) L_(B2) 184 L_(A80) L_(B2) 185 L_(A81) L_(B2) 186 L_(A82) L_(B2) 187 L_(A83) L_(B2) 188 L_(A84) L_(B2) 189 L_(A85) L_(B2) 190 L_(A86) L_(B2) 191 L_(A87) L_(B2) 192 L_(A88) L_(B2) 193 L_(A89) L_(B2) 194 L_(A90) L_(B2) 195 L_(A91) L_(B2) 196 L_(A92) L_(B2) 197 L_(A93) L_(B2) 198 L_(A94) L_(B2) 199 L_(A95) L_(B2) 200 L_(A96) L_(B2) 201 L_(A97) L_(B2) 202 L_(A98) L_(B2) 203 L_(A99) L_(B2) 204 L_(A100) L_(B2) 205 L_(A101) L_(B2) 206 L_(A102) L_(B2) 207 L_(A103) L_(B2) 208 L_(A104) L_(B2) 209 L_(A1) L_(B3) 210 L_(A2) L_(B3) 211 L_(A3) L_(B3) 212 L_(A4) L_(B3) 213 L_(A5) L_(B3) 214 L_(A6) L_(B3) 215 L_(A7) L_(B3) 216 L_(A8) L_(B3) 217 L_(A9) L_(B3) 218 L_(A10) L_(B3) 219 L_(A11) L_(B3) 220 L_(A12) L_(B3) 221 L_(A13) L_(B3) 222 L_(A14) L_(B3) 223 L_(A15) L_(B3) 224 L_(A16) L_(B3) 225 L_(A17) L_(B3) 226 L_(A18) L_(B3) 227 L_(A19) L_(B3) 228 L_(A20) L_(B3) 229 L_(A21) L_(B3) 230 L_(A22) L_(B3) 231 L_(A23) L_(B3) 232 L_(A24) L_(B3) 233 L_(A25) L_(B3) 234 L_(A26) L_(B3) 235 L_(A27) L_(B3) 236 L_(A28) L_(B3) 237 L_(A29) L_(B3) 238 L_(A30) L_(B3) 239 L_(A31) L_(B3) 240 L_(A32) L_(B3) 241 L_(A33) L_(B3) 242 L_(A34) L_(B3) 243 L_(A35) L_(B3) 244 L_(A36) L_(B3) 245 L_(A37) L_(B3) 246 L_(A38) L_(B3) 247 L_(A39) L_(B3) 248 L_(A40) L_(B3) 249 L_(A41) L_(B3) 250 L_(A42) L_(B3) 251 L_(A43) L_(B3) 252 L_(A44) L_(B3) 253 L_(A45) L_(B3) 254 L_(A46) L_(B3) 255 L_(A47) L_(B3) 256 L_(A48) L_(B3) 257 L_(A49) L_(B3) 258 L_(A50) L_(B3) 259 L_(A51) L_(B3) 260 L_(A52) L_(B3) 261 L_(A53) L_(B3) 262 L_(A54) L_(B3) 263 L_(A55) L_(B3) 264 L_(A56) L_(B3) 265 L_(A57) L_(B3) 266 L_(A58) L_(B3) 267 L_(A59) L_(B3) 268 L_(A60) L_(B3) 269 L_(A61) L_(B3) 270 L_(A62) L_(B3) 271 L_(A63) L_(B3) 272 L_(A64) L_(B3) 273 L_(A65) L_(B3) 274 L_(A66) L_(B3) 275 L_(A67) L_(B3) 276 L_(A68) L_(B3) 277 L_(A69) L_(B3) 278 L_(A70) L_(B3) 279 L_(A71) L_(B3) 280 L_(A72) L_(B3) 281 L_(A73) L_(B3) 282 L_(A74) L_(B3) 283 L_(A75) L_(B3) 284 L_(A76) L_(B3) 285 L_(A77) L_(B3) 286 L_(A78) L_(B3) 287 L_(A79) L_(B3) 288 L_(A80) L_(B3) 289 L_(A81) L_(B3) 290 L_(A82) L_(B3) 291 L_(A83) L_(B3) 292 L_(A84) L_(B3) 293 L_(A85) L_(B3) 294 L_(A86) L_(B3) 295 L_(A87) L_(B3) 296 L_(A88) L_(B3) 297 L_(A89) L_(B3) 298 L_(A90) L_(B3) 299 L_(A91) L_(B3) 300 L_(A92) L_(B3) 301 L_(A93) L_(B3) 302 L_(A94) L_(B3) 303 L_(A95) L_(B3) 304 L_(A96) L_(B3) 305 L_(A97) L_(B3) 306 L_(A98) L_(B3) 307 L_(A99) L_(B3) 308 L_(A100) L_(B3) 309 L_(A101) L_(B3) 310 L_(A102) L_(B3) 311 L_(A103) L_(B3) 312 L_(A104) L_(B3) 313 L_(A1) L_(B4) 314 L_(A2) L_(B4) 315 L_(A3) L_(B4) 316 L_(A4) L_(B4) 317 L_(A5) L_(B4) 318 L_(A6) L_(B4) 319 L_(A7) L_(B4) 320 L_(A8) L_(B4) 321 L_(A9) L_(B4) 322 L_(A10) L_(B4) 323 L_(A11) L_(B4) 324 L_(A12) L_(B4) 325 L_(A13) L_(B4) 326 L_(A14) L_(B4) 327 L_(A15) L_(B4) 328 L_(A16) L_(B4) 329 L_(A17) L_(B4) 330 L_(A18) L_(B4) 331 L_(A19) L_(B4) 332 L_(A20) L_(B4) 333 L_(A21) L_(B4) 334 L_(A22) L_(B4) 335 L_(A23) L_(B4) 336 L_(A24) L_(B4) 337 L_(A25) L_(B4) 338 L_(A26) L_(B4) 339 L_(A27) L_(B4) 340 L_(A28) L_(B4) 341 L_(A29) L_(B4) 342 L_(A30) L_(B4) 343 L_(A31) L_(B4) 344 L_(A32) L_(B4) 345 L_(A33) L_(B4) 346 L_(A34) L_(B4) 347 L_(A35) L_(B4) 348 L_(A36) L_(B4) 349 L_(A37) L_(B4) 350 L_(A38) L_(B4) 351 L_(A39) L_(B4) 352 L_(A40) L_(B4) 353 L_(A41) L_(B4) 354 L_(A42) L_(B4) 355 L_(A43) L_(B4) 356 L_(A44) L_(B4) 357 L_(A45) L_(B4) 358 L_(A46) L_(B4) 359 L_(A47) L_(B4) 360 L_(A48) L_(B4) 361 L_(A49) L_(B4) 362 L_(A50) L_(B4) 363 L_(A51) L_(B4) 364 L_(A52) L_(B4) 365 L_(A53) L_(B4) 366 L_(A54) L_(B4) 367 L_(A55) L_(B4) 368 L_(A56) L_(B4) 369 L_(A57) L_(B4) 370 L_(A58) L_(B4) 371 L_(A59) L_(B4) 372 L_(A60) L_(B4) 373 L_(A61) L_(B4) 374 L_(A62) L_(B4) 375 L_(A63) L_(B4) 376 L_(A64) L_(B4) 377 L_(A65) L_(B4) 378 L_(A66) L_(B4) 379 L_(A67) L_(B4) 380 L_(A68) L_(B4) 381 L_(A69) L_(B4) 382 L_(A70) L_(B4) 383 L_(A71) L_(B4) 384 L_(A72) L_(B4) 385 L_(A73) L_(B4) 386 L_(A74) L_(B4) 387 L_(A75) L_(B4) 388 L_(A76) L_(B4) 389 L_(A77) L_(B4) 390 L_(A78) L_(B4) 391 L_(A79) L_(B4) 392 L_(A80) L_(B4) 393 L_(A81) L_(B4) 394 L_(A82) L_(B4) 395 L_(A83) L_(B4) 396 L_(A84) L_(B4) 397 L_(A85) L_(B4) 398 L_(A86) L_(B4) 399 L_(A87) L_(B4) 400 L_(A88) L_(B4) 401 L_(A89) L_(B4) 402 L_(A90) L_(B4) 403 L_(A91) L_(B4) 404 L_(A92) L_(B4) 405 L_(A93) L_(B4) 406 L_(A94) L_(B4) 407 L_(A95) L_(B4) 408 L_(A96) L_(B4) 409 L_(A97) L_(B4) 410 L_(A98) L_(B4) 411 L_(A99) L_(B4) 412 L_(A100) L_(B4) 413 L_(A101) L_(B4) 414 L_(A102) L_(B4) 415 L_(A103) L_(B4) 416 L_(A104) L_(B4) 417 L_(A1) L_(B5) 418 L_(A2) L_(B5) 419 L_(A3) L_(B5) 420 L_(A4) L_(B5) 421 L_(A5) L_(B5) 422 L_(A6) L_(B5) 423 L_(A7) L_(B5) 424 L_(A8) L_(B5) 425 L_(A9) L_(B5) 426 L_(A10) L_(B5) 427 L_(A11) L_(B5) 428 L_(A12) L_(B5) 429 L_(A13) L_(B5) 430 L_(A14) L_(B5) 431 L_(A15) L_(B5) 432 L_(A16) L_(B5) 433 L_(A17) L_(B5) 434 L_(A18) L_(B5) 435 L_(A19) L_(B5) 436 L_(A20) L_(B5) 437 L_(A21) L_(B5) 438 L_(A22) L_(B5) 439 L_(A23) L_(B5) 440 L_(A24) L_(B5) 441 L_(A25) L_(B5) 442 L_(A26) L_(B5) 443 L_(A27) L_(B5) 444 L_(A28) L_(B5) 445 L_(A29) L_(B5) 446 L_(A30) L_(B5) 447 L_(A31) L_(B5) 448 L_(A32) L_(B5) 449 L_(A33) L_(B5) 450 L_(A34) L_(B5) 451 L_(A35) L_(B5) 452 L_(A36) L_(B5) 453 L_(A37) L_(B5) 454 L_(A38) L_(B5) 455 L_(A39) L_(B5) 456 L_(A40) L_(B5) 457 L_(A41) L_(B5) 458 L_(A42) L_(B5) 459 L_(A43) L_(B5) 460 L_(A44) L_(B5) 461 L_(A45) L_(B5) 462 L_(A46) L_(B5) 463 L_(A47) L_(B5) 464 L_(A48) L_(B5) 465 L_(A49) L_(B5) 466 L_(A50) L_(B5) 467 L_(A51) L_(B5) 468 L_(A52) L_(B5) 469 L_(A53) L_(B5) 470 L_(A54) L_(B5) 471 L_(A55) L_(B5) 472 L_(A56) L_(B5) 473 L_(A57) L_(B5) 474 L_(A58) L_(B5) 475 L_(A59) L_(B5) 476 L_(A60) L_(B5) 477 L_(A61) L_(B5) 478 L_(A62) L_(B5) 479 L_(A63) L_(B5) 480 L_(A64) L_(B5) 481 L_(A65) L_(B5) 482 L_(A66) L_(B5) 483 L_(A67) L_(B5) 484 L_(A68) L_(B5) 485 L_(A69) L_(B5) 486 L_(A70) L_(B5) 487 L_(A71) L_(B5) 488 L_(A72) L_(B5) 489 L_(A73) L_(B5) 490 L_(A74) L_(B5) 491 L_(A75) L_(B5) 492 L_(A76) L_(B5) 493 L_(A77) L_(B5) 494 L_(A78) L_(B5) 495 L_(A79) L_(B5) 496 L_(A80) L_(B5) 497 L_(A81) L_(B5) 498 L_(A82) L_(B5) 499 L_(A83) L_(B5) 500 L_(A84) L_(B5) 501 L_(A85) L_(B5) 502 L_(A86) L_(B5) 503 L_(A87) L_(B5) 504 L_(A88) L_(B5) 505 L_(A89) L_(B5) 506 L_(A90) L_(B5) 507 L_(A91) L_(B5) 508 L_(A92) L_(B5) 509 L_(A93) L_(B5) 510 L_(A94) L_(B5) 511 L_(A95) L_(B5) 512 L_(A96) L_(B5) 513 L_(A97) L_(B5) 514 L_(A98) L_(B5) 515 L_(A99) L_(B5) 516 L_(A100) L_(B5) 517 L_(A101) L_(B5) 518 L_(A102) L_(B5) 519 L_(A103) L_(B5) 520 L_(A104) L_(B5) 521 L_(A1) L_(B6) 522 L_(A2) L_(B6) 523 L_(A3) L_(B6) 524 L_(A4) L_(B6) 525 L_(A5) L_(B6) 526 L_(A6) L_(B6) 527 L_(A7) L_(B6) 528 L_(A8) L_(B6) 529 L_(A9) L_(B6) 530 L_(A10) L_(B6) 531 L_(A11) L_(B6) 532 L_(A12) L_(B6) 533 L_(A13) L_(B6) 534 L_(A14) L_(B6) 535 L_(A15) L_(B6) 536 L_(A16) L_(B6) 537 L_(A17) L_(B6) 538 L_(A18) L_(B6) 539 L_(A19) L_(B6) 540 L_(A20) L_(B6) 541 L_(A21) L_(B6) 542 L_(A22) L_(B6) 543 L_(A23) L_(B6) 544 L_(A24) L_(B6) 545 L_(A25) L_(B6) 546 L_(A26) L_(B6) 547 L_(A27) L_(B6) 548 L_(A28) L_(B6) 549 L_(A29) L_(B6) 550 L_(A30) L_(B6) 551 L_(A31) L_(B6) 552 L_(A32) L_(B6) 553 L_(A33) L_(B6) 554 L_(A34) L_(B6) 555 L_(A35) L_(B6) 556 L_(A36) L_(B6) 557 L_(A37) L_(B6) 558 L_(A38) L_(B6) 559 L_(A39) L_(B6) 560 L_(A40) L_(B6) 561 L_(A41) L_(B6) 562 L_(A42) L_(B6) 563 L_(A43) L_(B6) 564 L_(A44) L_(B6) 565 L_(A45) L_(B6) 566 L_(A46) L_(B6) 567 L_(A47) L_(B6) 568 L_(A48) L_(B6) 569 L_(A49) L_(B6) 570 L_(A50) L_(B6) 571 L_(A51) L_(B6) 572 L_(A52) L_(B6) 573 L_(A53) L_(B6) 574 L_(A54) L_(B6) 575 L_(A55) L_(B6) 576 L_(A56) L_(B6) 577 L_(A57) L_(B6) 578 L_(A58) L_(B6) 579 L_(A59) L_(B6) 580 L_(A60) L_(B6) 581 L_(A61) L_(B6) 582 L_(A62) L_(B6) 583 L_(A63) L_(B6) 584 L_(A64) L_(B6) 585 L_(A65) L_(B6) 586 L_(A66) L_(B6) 587 L_(A67) L_(B6) 588 L_(A68) L_(B6) 589 L_(A69) L_(B6) 590 L_(A70) L_(B6) 591 L_(A71) L_(B6) 592 L_(A72) L_(B6) 593 L_(A73) L_(B6) 594 L_(A74) L_(B6) 595 L_(A75) L_(B6) 596 L_(A76) L_(B6) 597 L_(A77) L_(B6) 598 L_(A78) L_(B6) 599 L_(A79) L_(B6) 600 L_(A80) L_(B6) 601 L_(A81) L_(B6) 602 L_(A82) L_(B6) 603 L_(A83) L_(B6) 604 L_(A84) L_(B6) 605 L_(A85) L_(B6) 606 L_(A86) L_(B6) 607 L_(A87) L_(B6) 608 L_(A88) L_(B6) 609 L_(A89) L_(B6) 610 L_(A90) L_(B6) 611 L_(A91) L_(B6) 612 L_(A92) L_(B6) 613 L_(A93) L_(B6) 614 L_(A94) L_(B6) 615 L_(A95) L_(B6) 616 L_(A96) L_(B6) 617 L_(A97) L_(B6) 618 L_(A98) L_(B6) 619 L_(A99) L_(B6) 620 L_(A100) L_(B6) 621 L_(A101) L_(B6) 622 L_(A102) L_(B6) 623 L_(A103) L_(B6) 624 L_(A104) L_(B6) 625 L_(A1) L_(B7) 626 L_(A2) L_(B7) 627 L_(A3) L_(B7) 628 L_(A4) L_(B7) 629 L_(A5) L_(B7) 630 L_(A6) L_(B7) 631 L_(A7) L_(B7) 632 L_(A8) L_(B7) 633 L_(A9) L_(B7) 634 L_(A10) L_(B7) 635 L_(A11) L_(B7) 636 L_(A12) L_(B7) 637 L_(A13) L_(B7) 638 L_(A14) L_(B7) 639 L_(A15) L_(B7) 640 L_(A16) L_(B7) 641 L_(A17) L_(B7) 642 L_(A18) L_(B7) 643 L_(A19) L_(B7) 644 L_(A20) L_(B7) 645 L_(A21) L_(B7) 646 L_(A22) L_(B7) 647 L_(A23) L_(B7) 648 L_(A24) L_(B7) 649 L_(A25) L_(B7) 650 L_(A26) L_(B7) 651 L_(A27) L_(B7) 652 L_(A28) L_(B7) 653 L_(A29) L_(B7) 654 L_(A30) L_(B7) 655 L_(A31) L_(B7) 656 L_(A32) L_(B7) 657 L_(A33) L_(B7) 658 L_(A34) L_(B7) 659 L_(A35) L_(B7) 660 L_(A36) L_(B7) 661 L_(A37) L_(B7) 662 L_(A38) L_(B7) 663 L_(A39) L_(B7) 664 L_(A40) L_(B7) 665 L_(A41) L_(B7) 666 L_(A42) L_(B7) 667 L_(A43) L_(B7) 668 L_(A44) L_(B7) 669 L_(A45) L_(B7) 670 L_(A46) L_(B7) 671 L_(A47) L_(B7) 672 L_(A48) L_(B7) 673 L_(A49) L_(B7) 674 L_(A50) L_(B7) 675 L_(A51) L_(B7) 676 L_(A52) L_(B7) 677 L_(A53) L_(B7) 678 L_(A54) L_(B7) 679 L_(A55) L_(B7) 680 L_(A56) L_(B7) 681 L_(A57) L_(B7) 682 L_(A58) L_(B7) 683 L_(A59) L_(B7) 684 L_(A60) L_(B7) 685 L_(A61) L_(B7) 686 L_(A62) L_(B7) 687 L_(A63) L_(B7) 688 L_(A64) L_(B7) 689 L_(A65) L_(B7) 690 L_(A66) L_(B7) 691 L_(A67) L_(B7) 692 L_(A68) L_(B7) 693 L_(A69) L_(B7) 694 L_(A70) L_(B7) 695 L_(A71) L_(B7) 696 L_(A72) L_(B7) 697 L_(A73) L_(B7) 698 L_(A74) L_(B7) 699 L_(A75) L_(B7) 700 L_(A76) L_(B7) 701 L_(A77) L_(B7) 702 L_(A78) L_(B7) 703 L_(A79) L_(B7) 704 L_(A80) L_(B7) 705 L_(A81) L_(B7) 706 L_(A82) L_(B7) 707 L_(A83) L_(B7) 708 L_(A84) L_(B7) 709 L_(A85) L_(B7) 710 L_(A86) L_(B7) 711 L_(A87) L_(B7) 712 L_(A88) L_(B7) 713 L_(A89) L_(B7) 714 L_(A90) L_(B7) 715 L_(A91) L_(B7) 716 L_(A92) L_(B7) 717 L_(A93) L_(B7) 718 L_(A94) L_(B7) 719 L_(A95) L_(B7) 720 L_(A96) L_(B7) 721 L_(A97) L_(B7) 722 L_(A98) L_(B7) 723 L_(A99) L_(B7) 724 L_(A100) L_(B7) 725 L_(A101) L_(B7) 726 L_(A102) L_(B7) 727 L_(A103) L_(B7) 728 L_(A104) L_(B7) 729 L_(A1) L_(B8) 730 L_(A2) L_(B8) 731 L_(A3) L_(B8) 732 L_(A4) L_(B8) 733 L_(A5) L_(B8) 734 L_(A6) L_(B8) 735 L_(A7) L_(B8) 736 L_(A8) L_(B8) 737 L_(A9) L_(B8) 738 L_(A10) L_(B8) 739 L_(A11) L_(B8) 740 L_(A12) L_(B8) 741 L_(A13) L_(B8) 742 L_(A14) L_(B8) 743 L_(A15) L_(B8) 744 L_(A16) L_(B8) 745 L_(A17) L_(B8) 746 L_(A18) L_(B8) 747 L_(A19) L_(B8) 748 L_(A20) L_(B8) 749 L_(A21) L_(B8) 750 L_(A22) L_(B8) 751 L_(A23) L_(B8) 752 L_(A24) L_(B8) 753 L_(A25) L_(B8) 754 L_(A26) L_(B8) 755 L_(A27) L_(B8) 756 L_(A28) L_(B8) 757 L_(A29) L_(B8) 758 L_(A30) L_(B8) 759 L_(A31) L_(B8) 760 L_(A32) L_(B8) 761 L_(A33) L_(B8) 762 L_(A34) L_(B8) 763 L_(A35) L_(B8) 764 L_(A36) L_(B8) 765 L_(A37) L_(B8) 766 L_(A38) L_(B8) 767 L_(A39) L_(B8) 768 L_(A40) L_(B8) 769 L_(A41) L_(B8) 770 L_(A42) L_(B8) 771 L_(A43) L_(B8) 772 L_(A44) L_(B8) 773 L_(A45) L_(B8) 774 L_(A46) L_(B8) 775 L_(A47) L_(B8) 776 L_(A48) L_(B8) 777 L_(A49) L_(B8) 778 L_(A50) L_(B8) 779 L_(A51) L_(B8) 780 L_(A52) L_(B8) 781 L_(A53) L_(B8) 782 L_(A54) L_(B8) 783 L_(A55) L_(B8) 784 L_(A56) L_(B8) 785 L_(A57) L_(B8) 786 L_(A58) L_(B8) 787 L_(A59) L_(B8) 788 L_(A60) L_(B8) 789 L_(A61) L_(B8) 790 L_(A62) L_(B8) 791 L_(A63) L_(B8) 792 L_(A64) L_(B8) 793 L_(A65) L_(B8) 794 L_(A66) L_(B8) 795 L_(A67) L_(B8) 796 L_(A68) L_(B8) 797 L_(A69) L_(B8) 798 L_(A70) L_(B8) 799 L_(A71) L_(B8) 800 L_(A72) L_(B8) 801 L_(A73) L_(B8) 802 L_(A74) L_(B8) 803 L_(A75) L_(B8) 804 L_(A76) L_(B8) 805 L_(A77) L_(B8) 806 L_(A78) L_(B8) 807 L_(A79) L_(B8) 808 L_(A80) L_(B8) 809 L_(A81) L_(B8) 810 L_(A82) L_(B8) 811 L_(A83) L_(B8) 812 L_(A84) L_(B8) 813 L_(A85) L_(B8) 814 L_(A86) L_(B8) 815 L_(A87) L_(B8) 816 L_(A88) L_(B8) 817 L_(A89) L_(B8) 818 L_(A90) L_(B8) 819 L_(A91) L_(B8) 820 L_(A92) L_(B8) 821 L_(A93) L_(B8) 822 L_(A94) L_(B8) 823 L_(A95) L_(B8) 824 L_(A96) L_(B8) 825 L_(A97) L_(B8) 826 L_(A98) L_(B8) 827 L_(A99) L_(B8) 828 L_(A100) L_(B8) 829 L_(A101) L_(B8) 830 L_(A102) L_(B8) 831 L_(A103) L_(B8) 832 L_(A104) L_(B8) 833 L_(A1) L_(B9) 834 L_(A2) L_(B9) 835 L_(A3) L_(B9) 836 L_(A4) L_(B9) 837 L_(A5) L_(B9) 838 L_(A6) L_(B9) 839 L_(A7) L_(B9) 840 L_(A8) L_(B9) 841 L_(A9) L_(B9) 842 L_(A10) L_(B9) 843 L_(A11) L_(B9) 844 L_(A12) L_(B9) 845 L_(A13) L_(B9) 846 L_(A14) L_(B9) 847 L_(A15) L_(B9) 848 L_(A16) L_(B9) 849 L_(A17) L_(B9) 850 L_(A18) L_(B9) 851 L_(A19) L_(B9) 852 L_(A20) L_(B9) 853 L_(A21) L_(B9) 854 L_(A22) L_(B9) 855 L_(A23) L_(B9) 856 L_(A24) L_(B9) 857 L_(A25) L_(B9) 858 L_(A26) L_(B9) 859 L_(A27) L_(B9) 860 L_(A28) L_(B9) 861 L_(A29) L_(B9) 862 L_(A30) L_(B9) 863 L_(A31) L_(B9) 864 L_(A32) L_(B9) 865 L_(A33) L_(B9) 866 L_(A34) L_(B9) 867 L_(A35) L_(B9) 868 L_(A36) L_(B9) 869 L_(A37) L_(B9) 870 L_(A38) L_(B9) 871 L_(A39) L_(B9) 872 L_(A40) L_(B9) 873 L_(A41) L_(B9) 874 L_(A42) L_(B9) 875 L_(A43) L_(B9) 876 L_(A44) L_(B9) 877 L_(A45) L_(B9) 878 L_(A46) L_(B9) 879 L_(A47) L_(B9) 880 L_(A48) L_(B9) 881 L_(A49) L_(B9) 882 L_(A50) L_(B9) 883 L_(A51) L_(B9) 884 L_(A52) L_(B9) 885 L_(A53) L_(B9) 886 L_(A54) L_(B9) 887 L_(A55) L_(B9) 888 L_(A56) L_(B9) 889 L_(A57) L_(B9) 890 L_(A58) L_(B9) 891 L_(A59) L_(B9) 892 L_(A60) L_(B9) 893 L_(A61) L_(B9) 894 L_(A62) L_(B9) 895 L_(A63) L_(B9) 896 L_(A64) L_(B9) 897 L_(A65) L_(B9) 898 L_(A66) L_(B9) 899 L_(A67) L_(B9) 900 L_(A68) L_(B9) 901 L_(A69) L_(B9) 902 L_(A70) L_(B9) 903 L_(A71) L_(B9) 904 L_(A72) L_(B9) 905 L_(A73) L_(B9) 906 L_(A74) L_(B9) 907 L_(A75) L_(B9) 908 L_(A76) L_(B9) 909 L_(A77) L_(B9) 910 L_(A78) L_(B9) 911 L_(A79) L_(B9) 912 L_(A80) L_(B9) 913 L_(A81) L_(B9) 914 L_(A82) L_(B9) 915 L_(A83) L_(B9) 916 L_(A84) L_(B9) 917 L_(A85) L_(B9) 918 L_(A86) L_(B9) 919 L_(A87) L_(B9) 920 L_(A88) L_(B9) 921 L_(A89) L_(B9) 922 L_(A90) L_(B9) 923 L_(A91) L_(B9) 924 L_(A92) L_(B9) 925 L_(A93) L_(B9) 926 L_(A94) L_(B9) 927 L_(A95) L_(B9) 928 L_(A96) L_(B9) 929 L_(A97) L_(B9) 930 L_(A98) L_(B9) 931 L_(A99) L_(B9) 932 L_(A100) L_(B9) 933 L_(A101) L_(B9) 934 L_(A102) L_(B9) 935 L_(A103) L_(B9) 936 L_(A104) L_(B9)

In some embodiments, the compound is selected from the group consisting of:

According to another aspect of the present disclosure, a first device is also provided. The first device includes a first organic light emitting device, that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer may include a host and a phosphorescent dopant. The emissive layer can include a compound having a structure according to formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z), and its variations as described herein.

The first device can be one or more of a consumer product, an organic light-emitting device and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.

The organic layer can also include a host. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of C_(n)H_(2n+1), OC_(n)H_(2n+1), OAr₁, N(C_(n)H_(2n+1))₂, N(Ar₁)(Ar₂), CH═CH—C_(n)H_(2n+1), C≡C—C_(n)H_(2n+1), Ar₁, Ar₁—Ar₂, C_(n)H_(2n)—Ar₁, or no substitution. In the preceding substituents n can range from 1 to 10; and Ar₁ and Ar₂ can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

The host can be a compound selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The host can include a metal complex. The host can be a specific compound selected from the group consisting of:

and combinations thereof.

In yet another aspect of the present disclosure, a formulation that comprises a compound having a structure according to formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z), and its variations as described herein is disclosed The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, and an electron transport layer material, disclosed herein.

Combination with Other Materials

The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

HIL/HTL:

A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but not limit to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoO_(x); a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.

Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:

Each of Ar¹ to Ar⁹ is selected from the group consisting aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; group consisting aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and group consisting 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Wherein each Ar is further substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, Ar¹ to Ar⁹ is independently selected from the group consisting of:

wherein k is an integer from 1 to 20; X¹⁰¹ to X¹⁰⁸ is C (including CH) or N; Z¹⁰¹ is NAr¹, O, or S; Ar¹ has the same group defined above.

Examples of metal complexes used in HIL or HTL include, but not limit to the following general formula:

wherein Met is a metal, which can have an atomic weight greater than 40; (Y¹⁰¹-Y¹⁰²) is a bidentate ligand, Y¹⁰¹ and Y¹⁰² are independently selected from C, N, O, P, and S; L¹⁰¹ is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, (Y¹⁰¹-Y¹⁰²) is a 2-phenylpyridine derivative. In another aspect, (Y¹⁰¹-Y¹⁰²) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc⁺/Fc couple less than about 0.6 V.

Host:

The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. While the Table below categorizes host materials as preferred for devices that emit various colors, any host material may be used with any dopant so long as the triplet criteria is satisfied.

Examples of metal complexes used as host are preferred to have the following general formula:

wherein Met is a metal; (Y¹⁰³-Y¹⁰⁴) is a bidentate ligand, Y¹⁰³ and Y¹⁰⁴ are independently selected from C, N, O, P, and S; L¹⁰¹ is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, the metal complexes are:

wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.

In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y¹⁰³-Y¹⁰⁴) is a carbene ligand.

Examples of organic compounds used as host are selected from the group consisting aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; group consisting aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and group consisting 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Wherein each group is further substituted by a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, host compound contains at least one of the following groups in the molecule:

wherein R¹⁰¹ to R¹⁰⁷ independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl heteroalkenyl alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20; k′″ is an integer from 0 to 20. X¹⁰¹ to X¹⁰⁸ is selected from C (including CH) or N. Z¹⁰¹ and Z¹⁰² is selected from NR¹⁰¹, O, or S.

HBL:

A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED.

In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.

In another aspect, compound used in HBL contains at least one of the following groups in the molecule:

wherein k is an integer from 1 to 20; L¹⁰¹ is an another ligand, k′ is an integer from 1 to 3.

ETL:

Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.

In one aspect, compound used in ETL contains at least one of the following groups in the molecule:

wherein R¹⁰¹ is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar¹ to Ar³ has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X¹⁰¹ to X¹⁰⁸ is selected from C (including CH) or N.

In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:

wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L¹⁰¹ is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.

In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. encompasses undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also encompass undeuterated, partially deuterated, and fully deuterated versions thereof.

In addition to and/or in combination with the materials disclosed herein, many hole injection materials, hole transporting materials, host materials, dopant materials, exiton/hole blocking layer materials, electron transporting and electron injecting materials may be used in an OLED. Non-limiting examples of the materials that may be used in an OLED in combination with materials disclosed herein are listed in Table A below. Table A lists non-limiting classes of materials, non-limiting examples of compounds for each class, and references that disclose the materials.

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EXPERIMENTAL Materials Synthesis

All reactions were carried out under nitrogen protections unless specified otherwise. All solvents for reactions are anhydrous and used as received from commercial sources.

Synthesis of Comparative Compound 1

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-5-phenylquinoline

Pd₂dba₃ (0.24 g, 0.26 mmol) dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SHOS) (0.43 g, 1.05 mmol), 5-chloro-2-(3,5-dimethylphenyl)quinoline (3.50 g, 13.1 mmol), phenylboronic acid (2.39 g, 19.6 mmol), and potassium phosphate (K₃PO₄) (5.55 g, 26.1 mmol) were diluted with 110 mL of dimethoxyethane (DME) and 22 mL of water. The solution was bubbled with nitrogen gas for 20 minutes and the reaction mixture was maintained at reflux for 12 hours. Upon completion, 100 mL of toluene was added and the mixture was extracted 3 times with 100 mL of dichloromethane (DCM), then dried over sodium sulfate, and evaporated. The crude product was purified via column chromatography using Heptanes/ethyl acetate (EA) (100/0 to 90/10) solvent system. The yellowish oil was solidified in heptanes. The filtered solids were triturated from methanol to afford the pure 2-(3,5-dimethylphenyl)-5-phenylquinoline (2.6 g, 65% yield).

Step 2:

Synthesis of Ir(III) Dimer

Iridium chloride hydrate (0.78 g, 2.10 mmol) and 2-(3,5-dimethylphenyl)-5-phenylquinoline (2.6 g, 8.40 mmol) were diluted in 24 ml 2-ethoxyethanol and 8 mL of water. The mixture was degassed by bubbling nitrogen for 20 minutes and the reaction was maintained at 105° C. for 24 hours. The reaction mixture was then cooled to 0° C. and filtered. The solid was washed with cold ethanol and dried to afford 1.6 g (85% yield) of the dimer.

Step 3:

Synthesis of Comparative Compound 1

A mixture of the Ir(III) dimer of step 2 (1.60 g, 0.95 mmol) from step 2, and 3,7-diethylnonane-4,6-dione (2.01 g, 9.47 mmol) were diluted in 20 mL 2-ethoxyethanol, and the mixture was degassed by bubbling nitrogen gas for 20 minutes. Potassium carbonate (1.31 g, 9.47 mmol) was then added and the reaction mixture was stirred at room temperature overnight. Upon completion, the reaction was diluted with dichloromethane (DCM), filtered through a pad of Celite and washed with more DCM. The crude material was purified via column chromatography (silica pre-treated with triethylamine) using a Heptanes/DCM (100/0 to 97/3) solvent system. The evaporated pure fractions were triturated in methanol which afforded 1.3 g (68% yield) of pure comparative compound 1.

Synthesis of Comparative Compound 2

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-5-(4-isopropylphenyl)quinoline

5-chloro-2-(3,5-dimethylphenyl)quinoline (3.75 g, 14.0 mmol), (4-isopropylphenyl)boronic acid (2.76 g, 16.8 mmol), Pd₂dba₃ (0.26 g, 0.28 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) (0.46 g, 1.12 mmol), and K₃PO₄ (5.95 g, 28.0 mmol) were diluted in toluene (120 mL) and water (25 mL). The mixture was degassed by bubbling nitrogen gas for 15 minutes and then the reaction mixture was refluxed overnight. Upon completion, the reaction mixture was cooled to room temperature, then extracted with toluene, and washed with water and brine. The crude product was purified via column chromatography using a heptanes/ethyl acetate (95/5) solvent system. The white powder was recrystallized from heptanes to isolate 2-(3,5-dimethylphenyl)-5-(4-isopropylphenyl)quinoline (3.0 g, 61% yield) as white crystals.

Step 2:

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-5-(4-isopropylphenyl)quinoline (1.10 g, 3.13 mmol) was solubilized in 2-ethoxyethanol (12 mL) and water (4 mL). The mixture was degassed with nitrogen for 30 minutes. Iridium chloride hydrate (0.36 g, 0.96 mmol) was then added to the solution (some ligand precipitated) and the reaction was refluxed under nitrogen for 24 h. After cooling, the solid was filtered, washed with methanol, and dried to yielded the Ir(III) dimer (0.65 g, 73% yield) as a dark red powder.

Step 3:

Synthesis of Comparative Compound 2

Ir(III) dimer of step 2 (0.65 g, 0.35 mmol) and pentane-2,4-dione (0.35 g, 3.50 mmol) were diluted in 2-Ethoxyethanol (12 mL). The mixture was then degassed by bubbling nitrogen gas through it. K₂CO₃ (0.48 g, 3.50 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM, filtered through a pad of Celite, and washed with DCM. The crude material was purified by column chromatography (silica pre-treated with TEA) using a heptanes/DCM (95/5 to 90/10)) solvent system. The combined fractions were triturated from methanol and the solids were recrystallized from DCM/methanol two times. Comparative compound 2 was isolated as a red powder. (0.4 g, 58% yield).

Synthesis of Comparative Compound 3

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-7-phenylquinoline

7-chloro-2-(3,5-dimethylphenyl)quinoline (3.5 g, 13.1 mmol), phenylboronic acid (2.39 g, 19.6 mmol), Pd₂dba₃ (0.24 g, 0.26 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.43 g, 1.05 mmol), and K₃PO₄ (5.55 g, 26.1 mmol) were inserted in a round bottom flask (RBF) and diluted with DME (110 mL) and Water (22 mL). The reaction was degassed by bubbling nitrogen gas for 15 minutes and then heated to reflux overnight. The mixture was then cooled to room temperature and extracted with ethyl alcohol (EA). The crude material was purified by column chromatography using a heptanes/EA (95/5) solvent system. The collected fractions were triturated with MeOH to afford 2-(3,5-dimethylphenyl)-5-phenylquinoline (3.4 g, 85% yield) as a white powder.

Step 2:

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-7-phenylquinoline (3.35 g, 10.8 mmol) was solubilized in ethoxyethanol (25 mL) and water (8 mL) and degassed by bubbling nitrogen gas for 30 minutes. Iridium chloride hydrate (1.00 g, 2.71 mmol) was then added to the mixture, which was then heated to reflux under nitrogen for 24 h. After cooling the mixture to room temperature, the solid was filtered, washed with methanol, and dried to give the Ir(III) Dimer (1.8 g 79% yield) as a red powder.

Step 3:

Synthesis of Comparative Compound 3

The Ir(III) dimer of step 2 (1.9 g, 1.13 mmol) and 3,7-diethylnonane-4,6-dione (2.39 g, 11.3 mmol) were diluted in 2-ethoxyethanol (40 mL), and the mixture was degassed by bubbling nitrogen gas for 15 minutes. Potassium carbonate (1.56 g, 11.3 mmol) was then added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the mixture was diluted with DCM, filtered through a plug of Celite, and washed with DCM. The crude material was purified by column chromatography (silica gel pre-treated with triethylamine) using a heptanes/DCM (95/5) solvent system. The collected fractions were titurated with MeOH. A red powder was recrystallized from a MeOH/DCM solvent system to afford 1.5 g (63% yield) of comparative compound 3 as red crystals.

Synthesis of Compound 28

Step 1:

Synthesis of Compound 28

Ir(III) dimer of step 2 of the synthesis of comparative compound 2 (1.50 g, 0.81 mmol), above, and 3,7-diethylnonane-4,6-dione (1.72 g, 8.1 mmol) were diluted in ethoxyethanol (27 mL). The mixture was then degassed by bubbling nitrogen gas. K₂CO (1.12 g, 8.1 mmol) was then added, and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM, filtered through a pad of Celite, and washed with DCM. The crude material was purified via column chromatography (silica pre-treated with triethylamine) using a heptanes/DCM 80/20 solvent system. The collected pure fractions were triturated from methanol, and the solids were recrystallized from DCM/methanol two times to yield compound 28 as dark red crystals (1.3 g, 73% yield).

Synthesis of Compound 80

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-7-(4-Isopropylphenyl)quinoline

7-chloro-2-(3,5-dimethylphenyl)quinoline (4.25 g, 15.9 mmol), (4-isopropylphenyl)boronic acid (3.12 g, 19.1 mmol), Pd₂dba₃ (0.29 g, 0.32 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) (0.52 g, 1.27 mmol), and K₃PO₄ (6.74 g, 31.7 mmol) were solubilized in toluene (130 mL) and water (27 mL). The reaction mixture was degassed by bubbling nitrogen gas through it for 15 minutes, then the reaction mixture was heated to reflux overnight. Upon completion, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and washed with brine and water. The crude product was purified via column chromatography using a heptanes/ethyl acetate (97/3 to 95/5) solvent system. The product was then recrystallized from heptanes/DCM to isolate 2-(3,5-dimethylphenyl)-7-(4-isopropylphenyl)quinoline (2.5 g, 45% yield) of pure ligand.

Step 2:

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-7-(4-isopropylphenyl)quinoline (2.25 g, 6.40 mmol) was solubilized in ethoxyethanol (23 mL) and water (8 mL), then the mixture was degassed with nitrogen gas for 30 minutes. Iridium chloride hydrate (0.68 g, 1.83 mmol) was then added to the reaction mixture, and the reaction mixture was refluxed under nitrogen for 24 h. After cooling to room temperature, the solid was filtered, washed with methanol and dried to give Ir(III) dimer (1.2 g, 71% yield) as a brown powder.

Step 3:

Synthesis of Compound 80

The Ir(III) dimer of step 2 (1.1 g, 0.59 mmol) and 3,7-diethylnonane-4,6-dione (1.26 g, 5.92 mmol) were diluted in ethoxyethanol (20 mL), then the reaction mixture was degassed by bubbling nitrogen gas through it. K₂CO (0.82 g, 5.92 mmol) was then added to the reaction mixture, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM, filtered through a pad of Celite, and washed with DCM. The crude material was purified by column chromatography (silica pre-treated with TEA) using a heptanes/DCM (95/5) solvent system. The collected pure fractions were triturated from methanol and the solids were recrystallized from DCM/MeOH. Compound 80 was isolate as a dark red solid (1.0 g, 76% yield).

Synthesis of Compound 81

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-7-(4-isobutylphenyl)quinoline

7-chloro-2-(3,5-dimethylphenyl)quinoline (3.5 g, 13.1 mmol), (4-isobutylphenyl)boronic acid (3.49 g, 19.6 mmol), Pd₂dba₃ (0.24 g, 0.26 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) (0.43 g, 1.05 mmol), and K₃PO₄ (5.55 g, 26.1 mmol) were diluted in toluene (110 mL) and water (20 mL). The reaction mixture was degassed by bubbling nitrogen through it for 15 minutes. The reaction mixture was then heated to reflux overnight. Upon completion, the mixture was cooled, extracted with EA and washed with water. The crude product was purified by column chromatography using a heptanes/EA (95/5) solvent system. The collected product was triturated from heptanes to isolate pure 2-(3,5-dimethylphenyl)-7-(4-isobutylphenyl)quinoline (3.10 g, 65% yield) as a white powder.

Step 2:

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-7-(4-isobutylphenyl)quinoline (3.2 g, 8.75 mmol) was solubilized in ethoxyethanol (27 mL) and water (9 mL), then degassed with nitrogen for 30 minutes. Iridium chloride hydrate (0.81 g, 2.19 mmol) was then added to the reaction mixture, and the reaction mixture was refluxed under nitrogen for 24 h. After cooling to room temperature, the solid was filtered, washed with methanol, and dried to give Ir(III) dimer (1.55 g, 74% yield) as a red powder. There was still ligand left, but the product was used without further purification.

Step 3:

Synthesis of Compound 81

The Ir(III) dimer of step 2 (1.50 g, 0.78 mmol) and 3,7-diethylnonane-4,6-dione (1.67 g, 7.84 mmol) were diluted in ethoxyethanol (26 mL), then the mixture was degassed by bubbling nitrogen gas through it. K₂CO₃ (1.08 g, 7.84 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM, filtered through a pad of Celite, and washed with DCM. The crude material was purified by column chromatography (silica pre-treated with TEA) using a heptanes/DCM (90/10) solvent system. The collected pure fractions were triturated from methanol and the solids were recrystallized from DCM/methanol. Compound 81 was isolated as a red powder (1.25 g, 70% yield).

Synthesis of Compound 84

Step 1:

Synthesis of 2-(3,5-dimethylphenyl)-7-(4-fluorophenyl)quinoline

7-chloro-2-(3,5-dimethylphenyl)quinoline (4 g, 14.94 mmol), (4-fluorophenyl)boronic acid (2.508 g, 17.93 mmol), Pd2(dba)3 (0.274 g, 0.299 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.491 g, 1.195 mmol), potassium phosphate (7.93 g, 37.3 mmol), toluene (100 mL) and water (20 mL) were combined in a flask. A condenser was attached then the system, which was evacuated and purged with nitrogen three times. The reaction mixture was heated to reflux overnight. After cooling, the reaction mixture was filtered through celite using ethyl acetate. After the aqueous was partitioned off, the organic portion was washed with brine once, dried with sodium sulfate, filtered, and concentrated down to 5.8 g of a brown solid. The sample was purified with silica gel using a heptane/DCM (50/50) solvent system to get 4.5 g of a white solid. HPLC indicated it was 99.7% pure. 125 ml heptane was added to the 4.5 g sample, then DCM until the solids dissolved. The solution was heated to reflux to remove the DCM. A white precipitate formed immediately upon cooling. The sample was allowed to stand for two hours, then the precipitate was filtered off to get 3.88 g of a white solid for a 79% yield of 2-(3,5-dimethylphenyl)-7-(4-fluorophenyl)quinoline.

Step 2:

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-7-(4-fluorophenyl)quinoline (3.00 g, 9.16 mmol) was solubilized in ethoxyethanol (29 mL) and water (10 mL), then the mixture was degassed with nitrogen for 30 minutes. Iridium chloride hydrate (0.85 g, 2.29 mmol) was then added to the reaction mixture, and the reaction mixture was refluxed under nitrogen for 24 h. After cooling to room temperature, the solid was filtered, washed with methanol, and dried to yield the Ir(III) dimer (2.70 g, 134% yield) as a red powder. There was still ligand left but the product was used without further purification. The true yield of the reaction is believed to be around 50-60%.

Step 3:

Synthesis of Compound 84

The Ir(III) dimer of step 2 (2.70 g, 1.53 mmol), 3,7-diethylnonane-4,6-dione (3.26 g, 15.3 mmol), and 2-ethoxyethanol (40 mL) were combined in a 100 ml single neck round bottom flask. Nitrogen was bubbled directly into the solution for 15 min. Potassium carbonate (2.12 g, 15.3 mmol) was added, then the system was placed under nitrogen and stirred at room temperature overnight. Next morning, TLC indicated a product had formed. The reaction was filtered through celite using DCM until the red color came off. The solution was concentrated down to a dark red oil. The sample was purified with silica gel, preconditioned with heptane/triethyl amine; DCM (60/20/20), then heptane/DCM (90/10), using a heptanes/DCM (90/10) solvent system. Fractions containing the dark red color were combined and concentrated down to 2.70 g of a dark red solid. To remove the ligand, the sample was triturated in 100 ml refluxing methanol, then the insoluble red precipitate was filtered off while the methanol was still hot to get 0.88 g of a red solid. The trituration was repeated with 75 ml hot methanol and the filtered red solid was dried in a vacuum oven overnight to get 0.80 g of a red solid for a 49.4% yield of compound 84.

Device Examples

All example devices were fabricated by high vacuum (<10⁻⁷ Torr) thermal evaporation. The anode electrode was 1200 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of LiF followed by 1,000 Å of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H₂O and O₂) immediately after fabrication, and a moisture getter was incorporated inside the package. The organic stack of the device examples consisted of sequentially, from the ITO surface, 100 Å of LG101 (purchased from LG chem) as the hole injection layer (HIL); 400 Å of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD) as the hole transporting layer (HTL); 300 Å of an emissive layer (EML) containing Compound H as a host (79%), a stability dopant (SD) (18%), and Compound 28, Compound 80, Compound 81, or Compound 84 as an emitter; 100 Å of Compound H as a blocking layer; and 450 Å of Alq₃ (tris-8-hydroxyquinoline aluminum) as the ETL. The emitter was selected to provide the desired color and the stability dopant (SD) was mixed with the electron-transporting host and the emitter to help transport positive charge in the emissive layer. The Comparative Example devices were fabricated similarly to the device examples except that Comparative Compounds 1, 2, and 3 were used as the emitter in the EML. Table 1 shows the composition of the EML in the device, while the device results and data are summarized in Table 2 and Table 3. As used herein, NPD, compound H, SD, and AlQ₃ have the following structures:

TABLE 1 Compounds of EML in the devices Example Emitter Device Compound 28 Example 1 Device Compound 80 Example 2 Device Compound 81 Example 3 Device Compound 84 Example 4 Comparative Comparative example 1 compound 1 Comparative Comparative example 2 compound 2 Comparative Comparative example 3 compound 3

TABLE 2 Device results of Device examples 1 and comparative device example 1. LE at λ 1,000 1931 CIE max FWHM nits x y [nm] [nm] [cd/A] Device 0.66 0.34 620 52 26.2 Example 1 Comparative 0.65 0.35 620 55 25.7 example 1 Comparative 0.65 0.35 622 61 21.8 example 2

TABLE 3 Device results of Device examples 2-4 and comparative device example 3 LE at λ 1,000 1931 CIE max FWHM nits x y [nm] [nm] [cd/A] Device 0.66 0.34 621 55 23.0 Example 2 Device 0.66 0.34 622 54 20.9 Example 3 Device 0.65 0.35 622 52 19.7 Example 4 Comparative 0.66 0.34 625 56 19.0 example 3

Tables 2 and 3 summarize the performance of the devices. The 1931 CIE values were measured at 10 mA/cm². The luminous efficiency was measured at 1000 cd/m². The device examples have a full width at half maximum (FWHM) that is narrower than the comparative examples. In addition, the devices with inventive compounds have higher luminous efficiency than the devices with comparative compounds. When compared against devices using comparative compounds 1 and 2 as emitter, device with inventive compound 28 as emitter showed narrow FWHM (52 nm vs. 55 nm and 61 nm) and higher efficiency. (26.2 cd/A vs. 25.7 cd/A and 21.8 cd/A). Device examples 2, 3, and 4 also show superior characteristics compared to comparative example 3.

It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting. 

We claim:
 1. A compound having a formula M(L_(A))_(x)(L_(B))(L_(C))_(z): wherein the ligand L_(A) is

wherein the ligand L_(B) is

wherein the ligand L_(C) is

wherein M is a metal having an atomic number greater than 40; wherein x is 1, or 2; wherein y is 1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein R¹, R², R³, and R⁴ are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl; wherein at least one of R¹, R², R³, and R⁴ has at least two C atoms; wherein R⁵ is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein R_(A), R_(C), and R_(D) each independently represent mono, di, tri, or tetra substitution, or no substitution; wherein R_(B) represents mono, di, tri, tetra, penta, or hexa substitution; wherein at least one R_(B) has the following structure:

wherein each of R_(A), R_(B), R_(C), and R_(D) are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substitutents of R_(A), R_(B), R_(C), and R_(D) are optionally joined to form a ring; wherein R⁶, R⁷, and R⁸ are independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof; and wherein at least one of R⁶, R⁷, and R⁸ is not hydrogen or deuterium.
 2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.
 3. The compound of claim 1, wherein M is Ir.
 4. The compound of claim 1, wherein ring A is benzene.
 5. The compound of claim 1, wherein ring C is benzene, and ring D is pyridine.
 6. The compound of claim 1, wherein R⁵ is selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.
 7. The compound of claim 1, wherein R⁵ is hydrogen.
 8. The compound of claim 1, wherein R¹, R², R³, and R⁴ are alkyl or cycloalkyl.
 9. The compound of claim 1, wherein R¹, R², R³, and R⁴ are independently selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.
 10. The compound of claim 1, wherein R⁶, R⁷, and R⁸ are independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, partially or fully fluorinated variants thereof, fluorine, and combinations thereof.
 11. The compound of claim 1, wherein R_(B) is mono substitution.
 12. The compound of claim 1, wherein the compound has the following formula:

wherein n is 1 or
 2. 13. The compound of claim 12, wherein n is
 2. 14. The compound of claim 12, wherein R_(A) is selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof.
 15. The compound of claim 12, wherein the compound has the following formula:

wherein R⁹, and R¹⁰ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof.
 16. The compound of claim 1, wherein L_(A) is selected from the group consisting of L_(A1) to L_(A104) listed below: L_(A1) through L_(A13), each represented by the formula

wherein in L_(A1): R⁷═CH₃, and R⁶═R⁸═H; in L_(A2): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A3): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A4): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A5): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A6): R⁷═F, and R⁶═R⁸═H; in L_(A7): R⁷═H, and R⁶═R₈═CH₃; in L_(A8): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A9): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A10): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A11): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A12): R⁷═H, and R⁶═R⁸═F; and in L_(A13): R⁶═R⁷═R⁸═CH₃; L_(A14) through L_(A26), each represented by the formula

wherein in L_(A14): R⁷═CH₃, and R⁶═R⁸═H; in L_(A14): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A16): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A17): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A18): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A19): R⁷═F, and R⁶═R⁸═H; in L_(A20): R⁷═H, and R⁶═R⁸═CH₃; in L_(A21): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A22): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A23): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A24): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A25): R⁷═H, and R⁶═R⁸═F; and in L_(A26): R⁶═R⁷═R⁸═CH₃; L_(A27) through L_(A39), each represented by the formula

wherein in L_(A27): R⁷═CH₃, and R⁶═R⁸═H; in L_(A28): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A29): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A30): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A31): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A32): R⁷═F, and R⁶═R⁸═H; in L_(A33): R⁷═H, and R⁶═R⁸═CH₃; in L_(A34): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A35): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A36): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A37): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A38): R⁷═H, and R⁶═R⁸═F; and in L_(A39): R⁶═R⁷═R⁸═CH₃; L_(A40) through L_(A52), each represented by the formula

wherein in L_(A40): R⁷═CH₃, and R⁶═R⁸═H; in L_(A41): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A42): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A43): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A44): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A45): R⁷═F, and R⁶═R⁸═H; in L_(A46): R⁷═H, and R⁶═R⁸═CH₃; in L_(A47): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A48): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A49): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A50): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A51): R⁷═H, and R⁶═R⁸═F; and in L_(A52): R⁶═R⁷═R⁸═CH₃; L_(A53) through L_(A65), each represented by the formula

wherein in L_(A53): R⁷═CH₃, and R⁶═R⁸═H; in L_(A54): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A55): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A56): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A57): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A58): R⁷═F, and R⁶═R⁸═H; in L_(A59): R⁷═H, and R⁶═R⁸═CH₃; in L_(A60): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A61): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A62): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A63): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A64): R⁷═H, and R⁶═R⁸═F; and in L_(A65): R⁶═R⁷═R⁸═CH₃; L_(A66) through L_(A78), each represented by the formula

wherein in L_(A66): R⁷═CH₃, and R⁶═R⁸═H; in L_(A67): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A68): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A69): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A70): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A71): R⁷═F, and R⁶═R⁸═H; in L_(A72): R⁷═H, and R⁶═R⁸═CH₃; in L_(A73): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A74): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A75): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A76): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A77): R⁷═H, and R⁶═R⁸═F; and in L_(A78): R⁶═R⁷═R⁸═CH₃; L_(A79) through L_(A91), each represented by the formula

wherein in L_(A79): R⁷═CH₃, and R⁶═R⁸═H; in L_(A80): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A81): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A82): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A83): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A84): R⁷═F, and R⁶═R⁸═H; in L_(A85): R⁷═H, and R⁶═R⁸═CH₃; in L_(A86): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A87): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A88): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A89): R⁷═H, and R⁶═R⁸ neopentyl; in L_(A90): R⁷═H, and R⁶═R⁸═F; and in L_(A91): R⁶═R⁷═R⁸═CH₃; and L_(A92) through L_(A104), each represented by the formula

wherein in L_(A92): R⁷═CH₃, and R⁶═R⁸═H; in L_(A93): R⁷=isopropyl, and R⁶═R⁸═H; in L_(A94): R⁷=isobutyl, and R⁶═R⁸═H; in L_(A95): R⁷=cyclopentyl, and R⁶═R⁸═H; in L_(A96): R⁷=neopentyl, and R⁶═R⁸═H; in L_(A97): R⁷═F, and R⁶═R⁸═H; in L_(A98): R⁷═H, and R⁶═R⁸═CH₃; in L_(A99): R⁷═H, and R⁶═R⁸=isopropyl; in L_(A100): R⁷═H, and R⁶═R⁸=isobutyl; in L_(A101): R⁷═H, and R⁶═R⁸=cyclopentyl; in L_(A102): R⁷═H, and R⁶═R⁸=neopentyl; in L_(A103): R⁷═H, and R⁶═R⁸═F; and in L_(A104): R⁶═R⁷═R⁸═CH₃.
 17. The compound of claim 1, wherein L_(B) is selected from the group consisting of L_(B1)-L_(B9) listed below:


18. The compound of claim 1, wherein the compound comprises ligand L_(A) and ligand L_(B) selected from the group consisting of: Compound Number L_(A) L_(B) 1 L_(A1) L_(B1) 2 L_(A2) L_(B1) 3 L_(A3) L_(B1) 4 L_(A4) L_(B1) 5 L_(A5) L_(B1) 6 L_(A6) L_(B1) 7 L_(A7) L_(B1) 8 L_(A8) L_(B1) 9 L_(A9) L_(B1) 10 L_(A10) L_(B1) 11 L_(A11) L_(B1) 12 L_(A12) L_(B1) 13 L_(A13) L_(B1) 14 L_(A14) L_(B1) 15 L_(A15) L_(B1) 16 L_(A16) L_(B1) 17 L_(A17) L_(B1) 18 L_(A18) L_(B1) 19 L_(A19) L_(B1) 20 L_(A20) L_(B1) 21 L_(A21) L_(B1) 22 L_(A22) L_(B1) 23 L_(A23) L_(B1) 24 L_(A24) L_(B1) 25 L_(A25) L_(B1) 26 L_(A26) L_(B1) 27 L_(A27) L_(B1) 28 L_(A28) L_(B1) 29 L_(A29) L_(B1) 30 L_(A30) L_(B1) 31 L_(A31) L_(B1) 32 L_(A32) L_(B1) 33 L_(A33) L_(B1) 34 L_(A34) L_(B1) 35 L_(A35) L_(B1) 36 L_(A36) L_(B1) 37 L_(A37) L_(B1) 38 L_(A38) L_(B1) 39 L_(A39) L_(B1) 40 L_(A40) L_(B1) 41 L_(A41) L_(B1) 42 L_(A42) L_(B1) 43 L_(A43) L_(B1) 44 L_(A44) L_(B1) 45 L_(A45) L_(B1) 46 L_(A46) L_(B1) 47 L_(A47) L_(B1) 48 L_(A48) L_(B1) 49 L_(A49) L_(B1) 50 L_(A50) L_(B1) 51 L_(A51) L_(B1) 52 L_(A52) L_(B1) 53 L_(A53) L_(B1) 54 L_(A54) L_(B1) 55 L_(A55) L_(B1) 56 L_(A56) L_(B1) 57 L_(A57) L_(B1) 58 L_(A58) L_(B1) 59 L_(A59) L_(B1) 60 L_(A60) L_(B1) 61 L_(A61) L_(B1) 62 L_(A62) L_(B1) 63 L_(A63) L_(B1) 64 L_(A64) L_(B1) 65 L_(A65) L_(B1) 66 L_(A66) L_(B1) 67 L_(A67) L_(B1) 68 L_(A68) L_(B1) 69 L_(A69) L_(B1) 70 L_(A70) L_(B1) 71 L_(A71) L_(B1) 72 L_(A72) L_(B1) 73 L_(A73) L_(B1) 74 L_(A74) L_(B1) 75 L_(A75) L_(B1) 76 L_(A76) L_(B1) 77 L_(A77) L_(B1) 78 L_(A78) L_(B1) 79 L_(A79) L_(B1) 80 L_(A80) L_(B1) 81 L_(A81) L_(B1) 82 L_(A82) L_(B1) 83 L_(A83) L_(B1) 84 L_(A84) L_(B1) 85 L_(A85) L_(B1) 86 L_(A86) L_(B1) 87 L_(A87) L_(B1) 88 L_(A88) L_(B1) 89 L_(A89) L_(B1) 90 L_(A90) L_(B1) 91 L_(A91) L_(B1) 92 L_(A92) L_(B1) 93 L_(A93) L_(B1) 94 L_(A94) L_(B1) 95 L_(A95) L_(B1) 96 L_(A96) L_(B1) 97 L_(A97) L_(B1) 98 L_(A98) L_(B1) 99 L_(A99) L_(B1) 100 L_(A100) L_(B1) 101 L_(A101) L_(B1) 102 L_(A102) L_(B1) 103 L_(A103) L_(B1) 104 L_(A104) L_(B1) 105 L_(A1) L_(B2) 106 L_(A2) L_(B2) 107 L_(A3) L_(B2) 108 L_(A4) L_(B2) 109 L_(A5) L_(B2) 110 L_(A6) L_(B2) 111 L_(A7) L_(B2) 112 L_(A8) L_(B2) 113 L_(A9) L_(B2) 114 L_(A10) L_(B2) 115 L_(A11) L_(B2) 116 L_(A12) L_(B2) 117 L_(A13) L_(B2) 118 L_(A14) L_(B2) 119 L_(A15) L_(B2) 120 L_(A16) L_(B2) 121 L_(A17) L_(B2) 122 L_(A18) L_(B2) 123 L_(A19) L_(B2) 124 L_(A20) L_(B2) 125 L_(A21) L_(B2) 126 L_(A22) L_(B2) 127 L_(A23) L_(B2) 128 L_(A24) L_(B2) 129 L_(A25) L_(B2) 130 L_(A26) L_(B2) 131 L_(A27) L_(B2) 132 L_(A28) L_(B2) 133 L_(A29) L_(B2) 134 L_(A30) L_(B2) 135 L_(A31) L_(B2) 136 L_(A32) L_(B2) 137 L_(A33) L_(B2) 138 L_(A34) L_(B2) 139 L_(A35) L_(B2) 140 L_(A36) L_(B2) 141 L_(A37) L_(B2) 142 L_(A38) L_(B2) 143 L_(A39) L_(B2) 144 L_(A40) L_(B2) 145 L_(A41) L_(B2) 146 L_(A42) L_(B2) 147 L_(A43) L_(B2) 148 L_(A44) L_(B2) 149 L_(A45) L_(B2) 150 L_(A46) L_(B2) 151 L_(A47) L_(B2) 152 L_(A48) L_(B2) 153 L_(A49) L_(B2) 154 L_(A50) L_(B2) 155 L_(A51) L_(B2) 156 L_(A52) L_(B2) 157 L_(A53) L_(B2) 158 L_(A54) L_(B2) 159 L_(A55) L_(B2) 160 L_(A56) L_(B2) 161 L_(A57) L_(B2) 162 L_(A58) L_(B2) 163 L_(A59) L_(B2) 164 L_(A60) L_(B2) 165 L_(A61) L_(B2) 166 L_(A62) L_(B2) 167 L_(A63) L_(B2) 168 L_(A64) L_(B2) 169 L_(A65) L_(B2) 170 L_(A66) L_(B2) 171 L_(A67) L_(B2) 172 L_(A68) L_(B2) 173 L_(A69) L_(B2) 174 L_(A70) L_(B2) 175 L_(A71) L_(B2) 176 L_(A72) L_(B2) 177 L_(A73) L_(B2) 178 L_(A74) L_(B2) 179 L_(A75) L_(B2) 180 L_(A76) L_(B2) 181 L_(A77) L_(B2) 182 L_(A78) L_(B2) 183 L_(A79) L_(B2) 184 L_(A80) L_(B2) 185 L_(A81) L_(B2) 186 L_(A82) L_(B2) 187 L_(A83) L_(B2) 188 L_(A84) L_(B2) 189 L_(A85) L_(B2) 190 L_(A86) L_(B2) 191 L_(A87) L_(B2) 192 L_(A88) L_(B2) 193 L_(A89) L_(B2) 194 L_(A90) L_(B2) 195 L_(A91) L_(B2) 196 L_(A92) L_(B2) 197 L_(A93) L_(B2) 198 L_(A94) L_(B2) 199 L_(A95) L_(B2) 200 L_(A96) L_(B2) 201 L_(A97) L_(B2) 202 L_(A98) L_(B2) 203 L_(A99) L_(B2) 204 L_(A100) L_(B2) 205 L_(A101) L_(B2) 206 L_(A102) L_(B2) 207 L_(A103) L_(B2) 208 L_(A104) L_(B2) 209 L_(A1) L_(B3) 210 L_(A2) L_(B3) 211 L_(A3) L_(B3) 212 L_(A4) L_(B3) 213 L_(A5) L_(B3) 214 L_(A6) L_(B3) 215 L_(A7) L_(B3) 216 L_(A8) L_(B3) 217 L_(A9) L_(B3) 218 L_(A10) L_(B3) 219 L_(A11) L_(B3) 220 L_(A12) L_(B3) 221 L_(A13) L_(B3) 222 L_(A14) L_(B3) 223 L_(A15) L_(B3) 224 L_(A16) L_(B3) 225 L_(A17) L_(B3) 226 L_(A18) L_(B3) 227 L_(A19) L_(B3) 228 L_(A20) L_(B3) 229 L_(A21) L_(B3) 230 L_(A22) L_(B3) 231 L_(A23) L_(B3) 232 L_(A24) L_(B3) 233 L_(A25) L_(B3) 234 L_(A26) L_(B3) 235 L_(A27) L_(B3) 236 L_(A28) L_(B3) 237 L_(A29) L_(B3) 238 L_(A30) L_(B3) 239 L_(A31) L_(B3) 240 L_(A32) L_(B3) 241 L_(A33) L_(B3) 242 L_(A34) L_(B3) 243 L_(A35) L_(B3) 244 L_(A36) L_(B3) 245 L_(A37) L_(B3) 246 L_(A38) L_(B3) 247 L_(A39) L_(B3) 248 L_(A40) L_(B3) 249 L_(A41) L_(B3) 250 L_(A42) L_(B3) 251 L_(A43) L_(B3) 252 L_(A44) L_(B3) 253 L_(A45) L_(B3) 254 L_(A46) L_(B3) 255 L_(A47) L_(B3) 256 L_(A48) L_(B3) 257 L_(A49) L_(B3) 258 L_(A50) L_(B3) 259 L_(A51) L_(B3) 260 L_(A52) L_(B3) 261 L_(A53) L_(B3) 262 L_(A54) L_(B3) 263 L_(A55) L_(B3) 264 L_(A56) L_(B3) 265 L_(A57) L_(B3) 266 L_(A58) L_(B3) 267 L_(A59) L_(B3) 268 L_(A60) L_(B3) 269 L_(A61) L_(B3) 270 L_(A62) L_(B3) 271 L_(A63) L_(B3) 272 L_(A64) L_(B3) 273 L_(A65) L_(B3) 274 L_(A66) L_(B3) 275 L_(A67) L_(B3) 276 L_(A68) L_(B3) 277 L_(A69) L_(B3) 278 L_(A70) L_(B3) 279 L_(A71) L_(B3) 280 L_(A72) L_(B3) 281 L_(A73) L_(B3) 282 L_(A74) L_(B3) 283 L_(A75) L_(B3) 284 L_(A76) L_(B3) 285 L_(A77) L_(B3) 286 L_(A78) L_(B3) 287 L_(A79) L_(B3) 288 L_(A80) L_(B3) 289 L_(A81) L_(B3) 290 L_(A82) L_(B3) 291 L_(A83) L_(B3) 292 L_(A84) L_(B3) 293 L_(A85) L_(B3) 294 L_(A86) L_(B3) 295 L_(A87) L_(B3) 296 L_(A88) L_(B3) 297 L_(A89) L_(B3) 298 L_(A90) L_(B3) 299 L_(A91) L_(B3) 300 L_(A92) L_(B3) 301 L_(A93) L_(B3) 302 L_(A94) L_(B3) 303 L_(A95) L_(B3) 304 L_(A96) L_(B3) 305 L_(A97) L_(B3) 306 L_(A98) L_(B3) 307 L_(A99) L_(B3) 308 L_(A100) L_(B3) 309 L_(A101) L_(B3) 310 L_(A102) L_(B3) 311 L_(A103) L_(B3) 312 L_(A104) L_(B3) 313 L_(A1) L_(B4) 314 L_(A2) L_(B4) 315 L_(A3) L_(B4) 316 L_(A4) L_(B4) 317 L_(A5) L_(B4) 318 L_(A6) L_(B4) 319 L_(A7) L_(B4) 320 L_(A8) L_(B4) 321 L_(A9) L_(B4) 322 L_(A10) L_(B4) 323 L_(A11) L_(B4) 324 L_(A12) L_(B4) 325 L_(A13) L_(B4) 326 L_(A14) L_(B4) 327 L_(A15) L_(B4) 328 L_(A16) L_(B4) 329 L_(A17) L_(B4) 330 L_(A18) L_(B4) 331 L_(A19) L_(B4) 332 L_(A20) L_(B4) 333 L_(A21) L_(B4) 334 L_(A22) L_(B4) 335 L_(A23) L_(B4) 336 L_(A24) L_(B4) 337 L_(A25) L_(B4) 338 L_(A26) L_(B4) 339 L_(A27) L_(B4) 340 L_(A28) L_(B4) 341 L_(A29) L_(B4) 342 L_(A30) L_(B4) 343 L_(A31) L_(B4) 344 L_(A32) L_(B4) 345 L_(A33) L_(B4) 346 L_(A34) L_(B4) 347 L_(A35) L_(B4) 348 L_(A36) L_(B4) 349 L_(A37) L_(B4) 350 L_(A38) L_(B4) 351 L_(A39) L_(B4) 352 L_(A40) L_(B4) 353 L_(A41) L_(B4) 354 L_(A42) L_(B4) 355 L_(A43) L_(B4) 356 L_(A44) L_(B4) 357 L_(A45) L_(B4) 358 L_(A46) L_(B4) 359 L_(A47) L_(B4) 360 L_(A48) L_(B4) 361 L_(A49) L_(B4) 362 L_(A50) L_(B4) 363 L_(A51) L_(B4) 364 L_(A52) L_(B4) 365 L_(A53) L_(B4) 366 L_(A54) L_(B4) 367 L_(A55) L_(B4) 368 L_(A56) L_(B4) 369 L_(A57) L_(B4) 370 L_(A58) L_(B4) 371 L_(A59) L_(B4) 372 L_(A60) L_(B4) 373 L_(A61) L_(B4) 374 L_(A62) L_(B4) 375 L_(A63) L_(B4) 376 L_(A64) L_(B4) 377 L_(A65) L_(B4) 378 L_(A66) L_(B4) 379 L_(A67) L_(B4) 380 L_(A68) L_(B4) 381 L_(A69) L_(B4) 382 L_(A70) L_(B4) 383 L_(A71) L_(B4) 384 L_(A72) L_(B4) 385 L_(A73) L_(B4) 386 L_(A74) L_(B4) 387 L_(A75) L_(B4) 388 L_(A76) L_(B4) 389 L_(A77) L_(B4) 390 L_(A78) L_(B4) 391 L_(A79) L_(B4) 392 L_(A80) L_(B4) 393 L_(A81) L_(B4) 394 L_(A82) L_(B4) 395 L_(A83) L_(B4) 396 L_(A84) L_(B4) 397 L_(A85) L_(B4) 398 L_(A86) L_(B4) 399 L_(A87) L_(B4) 400 L_(A88) L_(B4) 401 L_(A89) L_(B4) 402 L_(A90) L_(B4) 403 L_(A91) L_(B4) 404 L_(A92) L_(B4) 405 L_(A93) L_(B4) 406 L_(A94) L_(B4) 407 L_(A95) L_(B4) 408 L_(A96) L_(B4) 409 L_(A97) L_(B4) 410 L_(A98) L_(B4) 411 L_(A99) L_(B4) 412 L_(A100) L_(B4) 413 L_(A101) L_(B4) 414 L_(A102) L_(B4) 415 L_(A103) L_(B4) 416 L_(A104) L_(B4) 417 L_(A1) L_(B5) 418 L_(A2) L_(B5) 419 L_(A3) L_(B5) 420 L_(A4) L_(B5) 421 L_(A5) L_(B5) 422 L_(A6) L_(B5) 423 L_(A7) L_(B5) 424 L_(A8) L_(B5) 425 L_(A9) L_(B5) 426 L_(A10) L_(B5) 427 L_(A11) L_(B5) 428 L_(A12) L_(B5) 429 L_(A13) L_(B5) 430 L_(A14) L_(B5) 431 L_(A15) L_(B5) 432 L_(A16) L_(B5) 433 L_(A17) L_(B5) 434 L_(A18) L_(B5) 435 L_(A19) L_(B5) 436 L_(A20) L_(B5) 437 L_(A21) L_(B5) 438 L_(A22) L_(B5) 439 L_(A23) L_(B5) 440 L_(A24) L_(B5) 441 L_(A25) L_(B5) 442 L_(A26) L_(B5) 443 L_(A27) L_(B5) 444 L_(A28) L_(B5) 445 L_(A29) L_(B5) 446 L_(A30) L_(B5) 447 L_(A31) L_(B5) 448 L_(A32) L_(B5) 449 L_(A33) L_(B5) 450 L_(A34) L_(B5) 451 L_(A35) L_(B5) 452 L_(A36) L_(B5) 453 L_(A37) L_(B5) 454 L_(A38) L_(B5) 455 L_(A39) L_(B5) 456 L_(A40) L_(B5) 457 L_(A41) L_(B5) 458 L_(A42) L_(B5) 459 L_(A43) L_(B5) 460 L_(A44) L_(B5) 461 L_(A45) L_(B5) 462 L_(A46) L_(B5) 463 L_(A47) L_(B5) 464 L_(A48) L_(B5) 465 L_(A49) L_(B5) 466 L_(A50) L_(B5) 467 L_(A51) L_(B5) 468 L_(A52) L_(B5) 469 L_(A53) L_(B5) 470 L_(A54) L_(B5) 471 L_(A55) L_(B5) 472 L_(A56) L_(B5) 473 L_(A57) L_(B5) 474 L_(A58) L_(B5) 475 L_(A59) L_(B5) 476 L_(A60) L_(B5) 477 L_(A61) L_(B5) 478 L_(A62) L_(B5) 479 L_(A63) L_(B5) 480 L_(A64) L_(B5) 481 L_(A65) L_(B5) 482 L_(A66) L_(B5) 483 L_(A67) L_(B5) 484 L_(A68) L_(B5) 485 L_(A69) L_(B5) 486 L_(A70) L_(B5) 487 L_(A71) L_(B5) 488 L_(A72) L_(B5) 489 L_(A73) L_(B5) 490 L_(A74) L_(B5) 491 L_(A75) L_(B5) 492 L_(A76) L_(B5) 493 L_(A77) L_(B5) 494 L_(A78) L_(B5) 495 L_(A79) L_(B5) 496 L_(A80) L_(B5) 497 L_(A81) L_(B5) 498 L_(A82) L_(B5) 499 L_(A83) L_(B5) 500 L_(A84) L_(B5) 501 L_(A85) L_(B5) 502 L_(A86) L_(B5) 503 L_(A87) L_(B5) 504 L_(A88) L_(B5) 505 L_(A89) L_(B5) 506 L_(A90) L_(B5) 507 L_(A91) L_(B5) 508 L_(A92) L_(B5) 509 L_(A93) L_(B5) 510 L_(A94) L_(B5) 511 L_(A95) L_(B5) 512 L_(A96) L_(B5) 513 L_(A97) L_(B5) 514 L_(A98) L_(B5) 515 L_(A99) L_(B5) 516 L_(A100) L_(B5) 517 L_(A101) L_(B5) 518 L_(A102) L_(B5) 519 L_(A103) L_(B5) 520 L_(A104) L_(B5) 521 L_(A1) L_(B6) 522 L_(A2) L_(B6) 523 L_(A3) L_(B6) 524 L_(A4) L_(B6) 525 L_(A5) L_(B6) 526 L_(A6) L_(B6) 527 L_(A7) L_(B6) 528 L_(A8) L_(B6) 529 L_(A9) L_(B6) 530 L_(A10) L_(B6) 531 L_(A11) L_(B6) 532 L_(A12) L_(B6) 533 L_(A13) L_(B6) 534 L_(A14) L_(B6) 535 L_(A15) L_(B6) 536 L_(A16) L_(B6) 537 L_(A17) L_(B6) 538 L_(A18) L_(B6) 539 L_(A19) L_(B6) 540 L_(A20) L_(B6) 541 L_(A21) L_(B6) 542 L_(A22) L_(B6) 543 L_(A23) L_(B6) 544 L_(A24) L_(B6) 545 L_(A25) L_(B6) 546 L_(A26) L_(B6) 547 L_(A27) L_(B6) 548 L_(A28) L_(B6) 549 L_(A29) L_(B6) 550 L_(A30) L_(B6) 551 L_(A31) L_(B6) 552 L_(A32) L_(B6) 553 L_(A33) L_(B6) 554 L_(A34) L_(B6) 555 L_(A35) L_(B6) 556 L_(A36) L_(B6) 557 L_(A37) L_(B6) 558 L_(A38) L_(B6) 559 L_(A39) L_(B6) 560 L_(A40) L_(B6) 561 L_(A41) L_(B6) 562 L_(A42) L_(B6) 563 L_(A43) L_(B6) 564 L_(A44) L_(B6) 565 L_(A45) L_(B6) 566 L_(A46) L_(B6) 567 L_(A47) L_(B6) 568 L_(A48) L_(B6) 569 L_(A49) L_(B6) 570 L_(A50) L_(B6) 571 L_(A51) L_(B6) 572 L_(A52) L_(B6) 573 L_(A53) L_(B6) 574 L_(A54) L_(B6) 575 L_(A55) L_(B6) 576 L_(A56) L_(B6) 577 L_(A57) L_(B6) 578 L_(A58) L_(B6) 579 L_(A59) L_(B6) 580 L_(A60) L_(B6) 581 L_(A61) L_(B6) 582 L_(A62) L_(B6) 583 L_(A63) L_(B6) 584 L_(A64) L_(B6) 585 L_(A65) L_(B6) 586 L_(A66) L_(B6) 587 L_(A67) L_(B6) 588 L_(A68) L_(B6) 589 L_(A69) L_(B6) 590 L_(A70) L_(B6) 591 L_(A71) L_(B6) 592 L_(A72) L_(B6) 593 L_(A73) L_(B6) 594 L_(A74) L_(B6) 595 L_(A75) L_(B6) 596 L_(A76) L_(B6) 597 L_(A77) L_(B6) 598 L_(A78) L_(B6) 599 L_(A79) L_(B6) 600 L_(A80) L_(B6) 601 L_(A81) L_(B6) 602 L_(A82) L_(B6) 603 L_(A83) L_(B6) 604 L_(A84) L_(B6) 605 L_(A85) L_(B6) 606 L_(A86) L_(B6) 607 L_(A87) L_(B6) 608 L_(A88) L_(B6) 609 L_(A89) L_(B6) 610 L_(A90) L_(B6) 611 L_(A91) L_(B6) 612 L_(A92) L_(B6) 613 L_(A93) L_(B6) 614 L_(A94) L_(B6) 615 L_(A95) L_(B6) 616 L_(A96) L_(B6) 617 L_(A97) L_(B6) 618 L_(A98) L_(B6) 619 L_(A99) L_(B6) 620 L_(A100) L_(B6) 621 L_(A101) L_(B6) 622 L_(A102) L_(B6) 623 L_(A103) L_(B6) 624 L_(A104) L_(B6) 625 L_(A1) L_(B7) 626 L_(A2) L_(B7) 627 L_(A3) L_(B7) 628 L_(A4) L_(B7) 629 L_(A5) L_(B7) 630 L_(A6) L_(B7) 631 L_(A7) L_(B7) 632 L_(A8) L_(B7) 633 L_(A9) L_(B7) 634 L_(A10) L_(B7) 635 L_(A11) L_(B7) 636 L_(A12) L_(B7) 637 L_(A13) L_(B7) 638 L_(A14) L_(B7) 639 L_(A15) L_(B7) 640 L_(A16) L_(B7) 641 L_(A17) L_(B7) 642 L_(A18) L_(B7) 643 L_(A19) L_(B7) 644 L_(A20) L_(B7) 645 L_(A21) L_(B7) 646 L_(A22) L_(B7) 647 L_(A23) L_(B7) 648 L_(A24) L_(B7) 649 L_(A25) L_(B7) 650 L_(A26) L_(B7) 651 L_(A27) L_(B7) 652 L_(A28) L_(B7) 653 L_(A29) L_(B7) 654 L_(A30) L_(B7) 655 L_(A31) L_(B7) 656 L_(A32) L_(B7) 657 L_(A33) L_(B7) 658 L_(A34) L_(B7) 659 L_(A35) L_(B7) 660 L_(A36) L_(B7) 661 L_(A37) L_(B7) 662 L_(A38) L_(B7) 663 L_(A39) L_(B7) 664 L_(A40) L_(B7) 665 L_(A41) L_(B7) 666 L_(A42) L_(B7) 667 L_(A43) L_(B7) 668 L_(A44) L_(B7) 669 L_(A45) L_(B7) 670 L_(A46) L_(B7) 671 L_(A47) L_(B7) 672 L_(A48) L_(B7) 673 L_(A49) L_(B7) 674 L_(A50) L_(B7) 675 L_(A51) L_(B7) 676 L_(A52) L_(B7) 677 L_(A53) L_(B7) 678 L_(A54) L_(B7) 679 L_(A55) L_(B7) 680 L_(A56) L_(B7) 681 L_(A57) L_(B7) 682 L_(A58) L_(B7) 683 L_(A59) L_(B7) 684 L_(A60) L_(B7) 685 L_(A61) L_(B7) 686 L_(A62) L_(B7) 687 L_(A63) L_(B7) 688 L_(A64) L_(B7) 689 L_(A65) L_(B7) 690 L_(A66) L_(B7) 691 L_(A67) L_(B7) 692 L_(A68) L_(B7) 693 L_(A69) L_(B7) 694 L_(A70) L_(B7) 695 L_(A71) L_(B7) 696 L_(A72) L_(B7) 697 L_(A73) L_(B7) 698 L_(A74) L_(B7) 699 L_(A75) L_(B7) 700 L_(A76) L_(B7) 701 L_(A77) L_(B7) 702 L_(A78) L_(B7) 703 L_(A79) L_(B7) 704 L_(A80) L_(B7) 705 L_(A81) L_(B7) 706 L_(A82) L_(B7) 707 L_(A83) L_(B7) 708 L_(A84) L_(B7) 709 L_(A85) L_(B7) 710 L_(A86) L_(B7) 711 L_(A87) L_(B7) 712 L_(A88) L_(B7) 713 L_(A89) L_(B7) 714 L_(A90) L_(B7) 715 L_(A91) L_(B7) 716 L_(A92) L_(B7) 717 L_(A93) L_(B7) 718 L_(A94) L_(B7) 719 L_(A95) L_(B7) 720 L_(A96) L_(B7) 721 L_(A97) L_(B7) 722 L_(A98) L_(B7) 723 L_(A99) L_(B7) 724 L_(A100) L_(B7) 725 L_(A101) L_(B7) 726 L_(A102) L_(B7) 727 L_(A103) L_(B7) 728 L_(A104) L_(B7) 729 L_(A1) L_(B8) 730 L_(A2) L_(B8) 731 L_(A3) L_(B8) 732 L_(A4) L_(B8) 733 L_(A5) L_(B8) 734 L_(A6) L_(B8) 735 L_(A7) L_(B8) 736 L_(A8) L_(B8) 737 L_(A9) L_(B8) 738 L_(A10) L_(B8) 739 L_(A11) L_(B8) 740 L_(A12) L_(B8) 741 L_(A13) L_(B8) 742 L_(A14) L_(B8) 743 L_(A15) L_(B8) 744 L_(A16) L_(B8) 745 L_(A17) L_(B8) 746 L_(A18) L_(B8) 747 L_(A19) L_(B8) 748 L_(A20) L_(B8) 749 L_(A21) L_(B8) 750 L_(A22) L_(B8) 751 L_(A23) L_(B8) 752 L_(A24) L_(B8) 753 L_(A25) L_(B8) 754 L_(A26) L_(B8) 755 L_(A27) L_(B8) 756 L_(A28) L_(B8) 757 L_(A29) L_(B8) 758 L_(A30) L_(B8) 759 L_(A31) L_(B8) 760 L_(A32) L_(B8) 761 L_(A33) L_(B8) 762 L_(A34) L_(B8) 763 L_(A35) L_(B8) 764 L_(A36) L_(B8) 765 L_(A37) L_(B8) 766 L_(A38) L_(B8) 767 L_(A39) L_(B8) 768 L_(A40) L_(B8) 769 L_(A41) L_(B8) 770 L_(A42) L_(B8) 771 L_(A43) L_(B8) 772 L_(A44) L_(B8) 773 L_(A45) L_(B8) 774 L_(A46) L_(B8) 775 L_(A47) L_(B8) 776 L_(A48) L_(B8) 777 L_(A49) L_(B8) 778 L_(A50) L_(B8) 779 L_(A51) L_(B8) 780 L_(A52) L_(B8) 781 L_(A53) L_(B8) 782 L_(A54) L_(B8) 783 L_(A55) L_(B8) 784 L_(A56) L_(B8) 785 L_(A57) L_(B8) 786 L_(A58) L_(B8) 787 L_(A59) L_(B8) 788 L_(A60) L_(B8) 789 L_(A61) L_(B8) 790 L_(A62) L_(B8) 791 L_(A63) L_(B8) 792 L_(A64) L_(B8) 793 L_(A65) L_(B8) 794 L_(A66) L_(B8) 795 L_(A67) L_(B8) 796 L_(A68) L_(B8) 797 L_(A69) L_(B8) 798 L_(A70) L_(B8) 799 L_(A71) L_(B8) 800 L_(A72) L_(B8) 801 L_(A73) L_(B8) 802 L_(A74) L_(B8) 803 L_(A75) L_(B8) 804 L_(A76) L_(B8) 805 L_(A77) L_(B8) 806 L_(A78) L_(B8) 807 L_(A79) L_(B8) 808 L_(A80) L_(B8) 809 L_(A81) L_(B8) 810 L_(A82) L_(B8) 811 L_(A83) L_(B8) 812 L_(A84) L_(B8) 813 L_(A85) L_(B8) 814 L_(A86) L_(B8) 815 L_(A87) L_(B8) 816 L_(A88) L_(B8) 817 L_(A89) L_(B8) 818 L_(A90) L_(B8) 819 L_(A91) L_(B8) 820 L_(A92) L_(B8) 821 L_(A93) L_(B8) 822 L_(A94) L_(B8) 823 L_(A95) L_(B8) 824 L_(A96) L_(B8) 825 L_(A97) L_(B8) 826 L_(A98) L_(B8) 827 L_(A99) L_(B8) 828 L_(A100) L_(B8) 829 L_(A101) L_(B8) 830 L_(A102) L_(B8) 831 L_(A103) L_(B8) 832 L_(A104) L_(B8) 833 L_(A1) L_(B9) 834 L_(A2) L_(B9) 835 L_(A3) L_(B9) 836 L_(A4) L_(B9) 837 L_(A5) L_(B9) 838 L_(A6) L_(B9) 839 L_(A7) L_(B9) 840 L_(A8) L_(B9) 841 L_(A9) L_(B9) 842 L_(A10) L_(B9) 843 L_(A11) L_(B9) 844 L_(A12) L_(B9) 845 L_(A13) L_(B9) 846 L_(A14) L_(B9) 847 L_(A15) L_(B9) 848 L_(A16) L_(B9) 849 L_(A17) L_(B9) 850 L_(A18) L_(B9) 851 L_(A19) L_(B9) 852 L_(A20) L_(B9) 853 L_(A21) L_(B9) 854 L_(A22) L_(B9) 855 L_(A23) L_(B9) 856 L_(A24) L_(B9) 857 L_(A25) L_(B9) 858 L_(A26) L_(B9) 859 L_(A27) L_(B9) 860 L_(A28) L_(B9) 861 L_(A29) L_(B9) 862 L_(A30) L_(B9) 863 L_(A31) L_(B9) 864 L_(A32) L_(B9) 865 L_(A33) L_(B9) 866 L_(A34) L_(B9) 867 L_(A35) L_(B9) 868 L_(A36) L_(B9) 869 L_(A37) L_(B9) 870 L_(A38) L_(B9) 871 L_(A39) L_(B9) 872 L_(A40) L_(B9) 873 L_(A41) L_(B9) 874 L_(A42) L_(B9) 875 L_(A43) L_(B9) 876 L_(A44) L_(B9) 877 L_(A45) L_(B9) 878 L_(A46) L_(B9) 879 L_(A47) L_(B9) 880 L_(A48) L_(B9) 881 L_(A49) L_(B9) 882 L_(A50) L_(B9) 883 L_(A51) L_(B9) 884 L_(A52) L_(B9) 885 L_(A53) L_(B9) 886 L_(A54) L_(B9) 887 L_(A55) L_(B9) 888 L_(A56) L_(B9) 889 L_(A57) L_(B9) 890 L_(A58) L_(B9) 891 L_(A59) L_(B9) 892 L_(A60) L_(B9) 893 L_(A61) L_(B9) 894 L_(A62) L_(B9) 895 L_(A63) L_(B9) 896 L_(A64) L_(B9) 897 L_(A65) L_(B9) 898 L_(A66) L_(B9) 899 L_(A67) L_(B9) 900 L_(A68) L_(B9) 901 L_(A69) L_(B9) 902 L_(A70) L_(B9) 903 L_(A71) L_(B9) 904 L_(A72) L_(B9) 905 L_(A73) L_(B9) 906 L_(A74) L_(B9) 907 L_(A75) L_(B9) 908 L_(A76) L_(B9) 909 L_(A77) L_(B9) 910 L_(A78) L_(B9) 911 L_(A79) L_(B9) 912 L_(A80) L_(B9) 913 L_(A81) L_(B9) 914 L_(A82) L_(B9) 915 L_(A83) L_(B9) 916 L_(A84) L_(B9) 917 L_(A85) L_(B9) 918 L_(A86) L_(B9) 919 L_(A87) L_(B9) 920 L_(A88) L_(B9) 921 L_(A89) L_(B9) 922 L_(A90) L_(B9) 923 L_(A91) L_(B9) 924 L_(A92) L_(B9) 925 L_(A93) L_(B9) 926 L_(A94) L_(B9) 927 L_(A95) L_(B9) 928 L_(A96) L_(B9) 929 L_(A97) L_(B9) 930 L_(A98) L_(B9) 931 L_(A99) L_(B9) 932 L_(A100) L_(B9) 933 L_(A101) L_(B9) 934 L_(A102) L_(B9) 935 L_(A103) L_(B9) 936 L_(A104) L_(B9)


19. The compound of claim 1, wherein the compound is selected from the group consisting of


20. A first device comprising a first organic light emitting device, the first organic light emitting device comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z): wherein the ligand L_(A) is

wherein the ligand L_(B) is

wherein the ligand L_(C) is

wherein M is a metal having an atomic number greater than 40; wherein x is 1, or 2; wherein y is 1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein R¹, R², R³, and R⁴ are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl; wherein at least one of R¹, R², R³, and R⁴ has at least two C atoms; wherein R⁵ is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein R_(A), R_(C), and R_(D) each independently represent mono, di, tri, or tetra substitution, or no substitution; wherein R_(B) represents mono, di, tri, tetra, penta, or hexa substitution; wherein at least one R_(B) has the following structure:

wherein each of R_(A), R_(B), R_(C), and R_(D) are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substitutents of R_(A), R_(B), R_(C), and R_(D) are optionally joined to form a ring; wherein R⁶, R⁷, and R⁸ are independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof; and wherein at least one of R⁶, R⁷, and R⁸ is not hydrogen or deuterium.
 21. A formulation comprising a compound having a formula M(L_(A))_(x)(L_(B))_(y)(L_(C))_(z): wherein the ligand L_(A) is

wherein the ligand L_(B) is

wherein the ligand L_(C) is

wherein M is a metal having an atomic number greater than 40; wherein x is 1, or 2; wherein y is 1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein R¹, R², R³, and R⁴ are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl; wherein at least one of R¹, R², R³, and R⁴ has at least two C atoms; wherein R⁵ is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein rings A, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein R_(A), R_(C), and R_(D) each independently represent mono, di, tri, or tetra substitution, or no substitution; wherein R_(B) represents mono, di, tri, tetra, penta, or hexa substitution; wherein at least one R_(B) has the following structure:

wherein each of R_(A), R_(B), R_(C), and R_(D) are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substitutents of R_(A), R_(B), R_(C), and R_(D) are optionally joined to form a ring; wherein R⁶, R⁷, and R⁸ are independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halide, and combinations thereof; and wherein at least one of R⁶, R⁷, and R⁸ is not hydrogen or deuterium. 